Four‐Membered Rings Containing two Nitrogenc Heteroatoms
1983; Linguagem: Inglês
10.1002/9780470187197.ch3
ISSN1935-4665
Autores Tópico(s)Synthesis and Catalytic Reactions
ResumoChapter 3 Four-Membered Rings Containing two Nitrogenc Heteroatoms Reinhard Richter, Reinhard Richter The Upjohn Company, D. S. Gilmore Research Laboratories, North Haven, ConnecticutSearch for more papers by this authorHenri Ulrich, Henri Ulrich The Upjohn Company, D. S. Gilmore Research Laboratories, North Haven, ConnecticutSearch for more papers by this author Reinhard Richter, Reinhard Richter The Upjohn Company, D. S. Gilmore Research Laboratories, North Haven, ConnecticutSearch for more papers by this authorHenri Ulrich, Henri Ulrich The Upjohn Company, D. S. Gilmore Research Laboratories, North Haven, ConnecticutSearch for more papers by this author Book Editor(s):Alfred Hassner, Alfred Hassner Department of Chemistry, State University of New York at BinghamtonSearch for more papers by this author First published: 01 January 1983 https://doi.org/10.1002/9780470187197.ch3Citations: 4Book Series:Chemistry of Heterocyclic Compounds: A Series Of Monographs AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary This chapter contains sections titled: 1,2-Diazetines and 1,2-Diazetidines 1,3-Diazetidines References T. Curtius and J. Thun, J. Prakt. Chem., 44, 175 (1891). Google Scholar O. Hess, Ann. Chem., 232, 234 (1885). Google Scholar A compilation of earlier claims about the successful synthesis of 1,2-diazetes, 1,2-diazetines, and 1,2-diazetidines, together with the results of newer investigations, can be found in J. A. Moore, Trimethyleneimines, in A. Weissberger, Ed., Heterocyclic Compounds with Three and Fourmembered Rings, Part 2, Interscience, New York-London-Sydney, 1964, p. 885. Google Scholar H. Staudinger, Die Ketene, F. Enke, Stuttgart, 1912, p. 591. Google Scholar J. C. Stowell, J. Org. Chem., 32, 2360 (1967). 10.1021/jo01282a064 CASWeb of Science®Google Scholar D. Horovitz, U.S. Patent 3,129,215 (1964) to FMC Corp.; Google Scholar Chem. Abstr., 60, 15874 (1964). Google Scholar J. H. Hall and W. S. Bigard, J. Org. Chem., 43, 2785 (1978). 10.1021/jo00408a009 CASWeb of Science®Google Scholar H. Emeleus and G. L. Hurst, J. Chem. Soc., 3276 (1962). Google Scholar (a) E. Koerner von Gustorf, D. V. White, B. Kim, D. Hess, and J. Leitich, J. Org. Chem., 35, 1155 (1970); 10.1021/jo00829a065 Web of Science®Google Scholar(b) A. Hassner, D. Y. Tang, and J. Keogh, J. Org. Chem., 41, 2102 (1976). 10.1021/jo00874a007 CASWeb of Science®Google Scholar J. Firl and S. Sommer, Tetrahedron Lett., 1929 (1970). Google Scholar K. Adler and H. Niklas, Ann. Chem., 585, 97 (1954). 10.1002/jlac.19545850110 Google Scholar J. Firl and S. Sommer, Tetrahedron Lett., 1133 (1969). Google Scholar J. Firl and S. Sommer, Tetrahedron Lett., 1137 (1969). Google Scholar R. D. Cramer, U.S. Patent 2,456,176 (1948); Google Scholar Chem. Abstr., 43, 3445 (1949). Google Scholar J. C. Kauer and A. K. Schneider, J. Am. Chem. Soc., 82, 852 (1960). 10.1021/ja01489a022 CASWeb of Science®Google Scholar M. A. Englin, A. S. Filatov, and N. F. Sirotenkova, Zh. Org. Khim., 5, 1597 (1969). Google Scholar S. A. Rodkin, A. Y. Yakubovich, and S. P. Makarov, Zh. Org. Khim., 7, 2271 (1971). Web of Science®Google Scholar E. E. Nunn and R. N. Warrener, J. Chem. Soc., Chem. Commun., 818 (1972). Google Scholar G. Ahlgren and B. Akermark, Acta Chem. Scand., 21, 2910 (1967). 10.3891/acta.chem.scand.21-2910 CASWeb of Science®Google Scholar O. Diels and K. Alder, Ann. Chem., 450, 237 (1926). 10.1002/jlac.19264500119 CASGoogle Scholar C. F. Huebner, P. L. Strachan, E. M. Donoghue, N. Cahoon, L. Dorfman, R. Margerison, and E. Wenkert, J. Org. Chem., 32, 1126 (1967). 10.1021/jo01279a060 CASWeb of Science®Google Scholar E. Koener von Gustorf and B. Kim, Angew. Chem., 76, 592 (1964). 10.1002/ange.19640761383 Google Scholar C. F. Huebner, E. M. Donoghue, C. J. Novak, L. Dorfman, and E. Wenkert, J. Org. Chem., 35, 1149 (1970). 10.1021/jo00829a064 CASWeb of Science®Google Scholar (a) R. A. Clement, J. Org. Chem., 25, 1724 (1960); 10.1021/jo01080a011 CASWeb of Science®Google Scholar J. Org. Chem., 27, 1115 (1962); 10.1021/jo01051a001 CASWeb of Science®Google Scholar(b) T. J. Kealy, J. Am. Chem. Soc., 84, 966 (1962). 10.1021/ja00865a018 CASWeb of Science®Google Scholar O. L. Chapman and S. J. Dominianni, J. Org. Chem., 31, 3862 (1966). 10.1021/jo01349a518 CASWeb of Science®Google Scholar M. Lora-Tamayo, P. Navarro, and J. L. Soto, Ann. Chem., 748, 96 (1971). 10.1002/jlac.19717480111 CASGoogle Scholar R. E. Putnam, J. L. Anderson, and W. H. Sharkey, J. Am. Chem. Soc., 83, 386 (1961). 10.1021/ja01463a031 CASWeb of Science®Google Scholar D. J. Pasto and A. Fu-Taichen, Tetrahedron Lett., 2995 (1972). Google Scholar E. A. Wildi and B. K. Carpenter, Tetrahedron Lett., 2469 (1978). Google Scholar L. J. Altman, M. F. Semmelhack, R. B. Hornby, and J. C. Vederas, J. Chem. Soc., Chem. Commun., 686 (1968). Google Scholar S. Sommer, Tetrahedron Lett., 117 (1977). Google Scholar S. Sommer and U. Schubert, Angew. Chem., 91, 757 (1979). 10.1002/ange.19790910930 CASGoogle Scholar K. B. Wagener, S. R. Turner, and G. B. Butler, J. Org. Chem., 37, 1454 (1972). 10.1021/jo00974a042 CASWeb of Science®Google Scholar J. Firl and S. Sommer, Tetrahedron Lett., 1925 (1970). Google Scholar S. R. Turner, L. J. Giulbault, and G. B. Butler, J. Org. Chem., 36, 2838 (1971). 10.1021/jo00818a024 Web of Science®Google Scholar J. Firl and S. Sommer, Tetrahedron Lett., 4713 (1972). Google Scholar L. Marchetti and G. Tosi, Tetrahedron Lett., 3071 (1971). Google Scholar R. H. Rynbrandt, J. Heterocyclic Chem., 11, 787 (1974). 10.1002/jhet.5570110523 CASWeb of Science®Google Scholar F. Effenberger, unpublished results. Google Scholar F. Effenberger and R. Maier, Angew. Chem. Int. Ed., 5, 416 (1966). 10.1002/anie.196604162 CASWeb of Science®Google Scholar D. H. Clemens, J. A. Bell, and J. L. O'Brian, J. Org. Chem., 29, 2932 (1964). 10.1021/jo01033a030 CASWeb of Science®Google Scholar F. Effenberger, R. Gleiter, and G. Kiefer, Chem. Ber., 99, 3892 (1966). 10.1002/cber.19660991222 CASWeb of Science®Google Scholar J. H. Hall and M. Wojciechowska, J. Org. Chem., 43, 3348 (1978). 10.1021/jo00411a019 CASWeb of Science®Google Scholar J. H. Hall and M. Wojciechowska, J. Org. Chem., 43, 4869 (1978). 10.1021/jo00419a034 CASWeb of Science®Google Scholar J. Sauer, D. Lang, and H. Wiest, Chem. Ber., 97, 3208 (1964). 10.1002/cber.19640971130 CASWeb of Science®Google Scholar (a) R. W. Hoffmann, U. Bressel, J. Gehlhaus, and H. Häuser, Chem. Ber., 104, 873 (1971); 10.1002/cber.19711040324 CASWeb of Science®Google Scholar(b) R. W. Hoffmann and H. Häuser, Angew. Chem. Int. Ed., 3, 380 (1964). 10.1002/anie.196403801 Web of Science®Google Scholar C. K. Ingold and S. D. Weaver, J. Chem. Soc., 127, 378 (1925). 10.1039/ct9252700378 CASWeb of Science®Google Scholar A. H. Cook and D. G. Jones, J. Chem. Soc., 184 (1941). Google Scholar J. H. Hall and R. Kellog, J. Org. Chem., 31, 1079 (1966). 10.1021/jo01342a021 CASWeb of Science®Google Scholar R. C. Kerber, T. J. Ryan, and S. D. Hsu, J. Org. Chem., 39, 1215 (1974). 10.1021/jo00923a011 CASWeb of Science®Google Scholar R. C. Kerber and T. J. Ryan, Tetrahedron Lett., 703 (1970). Google Scholar D. Y. Curtin and J. L. Tveten, J. Org. Chem., 26, 1764 (1961). 10.1021/jo01065a017 CASWeb of Science®Google Scholar G. O. Schenck and N. Engelhard, Angew. Chem., 68, 71 (1956). 10.1002/ange.19560680214 CASWeb of Science®Google Scholar S. Skraup and O. Binder, Chem. Ber., 62, 1127 (1929). 10.1002/cber.19290620506 Google Scholar G. Brooks, M. A. Shah, and G. A. Taylor, J. Chem. Soc. Perkin, I, 1297 (1973). 10.1039/p19730001297 Web of Science®Google Scholar M. Colonna and A. Risaliti, Gazz. Chim. Ital., 90, 1165 (1960). CASGoogle Scholar C. W. Bird, Tetrahedron, 21, 2179 (1965). 10.1016/S0040-4020(01)98354-1 CASWeb of Science®Google Scholar L. Horner, E. Spietschka, and A. Gross, Ann. Chem., 573, 17 (1951). 10.1002/jlac.19515730103 CASWeb of Science®Google Scholar W. Fischer and E. Fahr, Tetrahedron Lett., 5245 (1966). Google Scholar S. Sommer, Angew. Chem. Int. Ed., 15, 432 (1976). 10.1002/anie.197604321 Web of Science®Google Scholar S. Sommer, Angew. Chem. Int. Ed., 16, 58 (1977). 10.1002/anie.197700581 Web of Science®Google Scholar E. Fahr, W. Fischer, A. Jung, L. Sauer, and A. Mannschreck, Tetrahedron Lett., 161 (1967). Google Scholar R. Huisgen and H.-U. Reissig, J. Chem. Soc., Chem. Commun., 568 (1979). Google Scholar W. Ried and E. Kahr, Chem. Ber., 103, 331 (1970). 10.1002/cber.19701030203 CASGoogle Scholar T. Eicher and E. V. Angerer, Chem. Ber., 103, 339 (1970). 10.1002/cber.19701030204 CASWeb of Science®Google Scholar W. Ried and R. Dietrich, Ann. Chem., 666, 113 (1963). 10.1002/jlac.19636660116 CASWeb of Science®Google Scholar W. Ried and R. Kraerner, Ann. Chem., 681, 52 (1965). 10.1002/jlac.19656810111 CASWeb of Science®Google Scholar C. W. Bird, J. Chem. Soc., 5284 (1964). Google Scholar C. W. Bird and T. D. Twibell, Tetrahedron, 28, 2813 (1972). 10.1016/0040-4020(72)80117-0 CASWeb of Science®Google Scholar C. W. Bird, M. W. Kaczmar, and C. K. Wong, Tetrahedron, 30, 2549 (1974). 10.1016/S0040-4020(01)97130-3 CASWeb of Science®Google Scholar M. W. Barker and M. E. Coker, J. Heterocyclic Chem., 4, 155 (1967). 10.1002/jhet.5570040135 CASWeb of Science®Google Scholar M. W. Barker and R. H. Jones, J. Heterocyclic Chem., 9, 555 (1972). 10.1002/jhet.5570090316 CASWeb of Science®Google Scholar M. W. Barker, S. Perumal, and C. J. Wierengo, J. Heterocyclic Chem., 11, 409, (1974). 10.1002/jhet.5570110327 CASWeb of Science®Google Scholar R. W. Hoffmann and W. Schäfer, Chem. Ber., 105, 2437 (1972). 10.1002/cber.19721050803 CASWeb of Science®Google Scholar W. H. Knoth and D. D. Coffman, J. Am. Chem. Soc., 82, 3873 (1960). 10.1021/ja01500a022 CASWeb of Science®Google Scholar S. Searles, Jr. and R. A. Clasen, Tetrahedron Lett., 1627 (1965). Google Scholar P. H. Ogden, J. Chem. Soc. (C), 2920 (1970). Google Scholar A. Padwa, W. Bergmark, and D. Pashayan, J. Am. Chem. Soc., 90, 4458 (1968). 10.1021/ja01018a048 CASWeb of Science®Google Scholar G. Balogh and F. C. De Schryver, Tetrahedron Lett., 1371 (1969). Google Scholar R. O. Kan and R. L. Furey, J. Am. Chem. Soc., 90, 1666 (1968) assigned a wrong 1,3-diazetidine structure to these products. 10.1021/ja01008a057 CASWeb of Science®Google Scholar J. G. Smith, Can. J. Chem., 44, 59 (1966). 10.1139/v66-010 CASWeb of Science®Google Scholar W. Schlenk and E. Bergmann, Ann. Chem., 463, 32 (1928). 10.1002/jlac.19284630102 Google Scholar Y. Jean and A. Devaquet, J. Am. Chem. Soc., 99, 1949 (1977). Google Scholar F. W. Fowler, J. Org. Chem., 37, 1321 (1972). 10.1021/jo00974a009 Web of Science®Google Scholar W. R. Dolbier, Jr. and W. M. Williams, J. Am. Chem. Soc., 91, 2818 (1969). 10.1021/ja01038a090 CASWeb of Science®Google Scholar W. M. Williams and W. R. Dolbier, Jr., J. Am. Chem. Soc., 94, 3955 (1972). 10.1021/ja00766a050 CASWeb of Science®Google Scholar G. L. Closs and W. A. Böll, J. Am. Chem. Soc., 85, 3904 (1963). 10.1021/ja00906a050 CASWeb of Science®Google Scholar G. L. Closs, W. A. Böll, H. Heyn, and V. Dev, J. Am. Chem. Soc., 90, 173 (1968). 10.1021/ja01003a030 CASWeb of Science®Google Scholar W. J. Leigh and D. R. Arnold, Can. J. Chem., 57, 1186 (1979). 10.1139/v79-194 CASWeb of Science®Google Scholar A. A. Reid, J. T. Sharp, and S. J. Murray, J. Chem. Soc., Chem. Commun., 827 (1972). Google Scholar A. A. Reid, H. R. Sood, and J. T. Sharp, J. Chem. Soc. Perkin, I, 362 (1976). 10.1039/p19760000362 Web of Science®Google Scholar M. Pomerantz and G. W. Gruber, J. Am. Chem. Soc., 93, 6615 (1971). 10.1021/ja00753a048 CASWeb of Science®Google Scholar R. McEwan and J. T. Sharp, J. Chem. Soc., Chem. Commun., 85 (1973). Google Scholar M. A. Battiste and T. J. Barton, Tetrahedron Lett., 1227 (1967). Google Scholar (a) J. Sauer and G. Heinrichs, Tetrahedron Lett., 4979 (1966); Google Scholar(b) G. Heinrichs, H. Krapf, B. Schröder, A. Steigel, T. Troll, and J. Sauer, Tetrahedron Lett., 1617 (1970). Google Scholar C. D. Anderson, J. H. Sharp, E. Stefaniuk, and R. S. Strathdee, Tetrahedron Lett., 305 (1976). Google Scholar T. Tsuchiya and J. Kurita, J. Chem. Soc., Chem. Commun., 803 (1979). Google Scholar D. J. Anderson and A. Hassner, J. Chem. Soc., Chem. Commun., 45 (1974). Google Scholar W. Berning and S. Hünig, Angew. Chem. Int. Ed., 16, 777 (1977). 10.1002/anie.197707772 Web of Science®Google Scholar S. F. Nelson, C. R. Kessel, and H. N. Brace, J. Am. Chem. Soc., 101, 1874 (1979). 10.1021/ja00501a039 Web of Science®Google Scholar J. A. Deyrup, Tetrahedron Lett., 2191 (1971). Google Scholar P. Robson, V. C. R. McLoughlin, J. B. Hynes, and L. C. Bigelow, J. Am. Chem. Soc., 83, 5010 (1961). 10.1021/ja01485a030 CASWeb of Science®Google Scholar E. A. V. Ebsworth and G. L. Hurst, J. Chem. Soc., 4840 (1962). Google Scholar J. L. Gerlock, E. G. Janzen, and J. F. Ruff, J. Am. Chem. Soc., 92, 2558 (1970). 10.1021/ja00711a065 CASWeb of Science®Google Scholar I. V. Vereshchinskii and A. T. Podkhalyuzin, Dokl. Akad. Nauk SSSR, 165, 107 (1965); Web of Science®Google Scholar Chem. Abstr., 64, 5060 (1966). Google Scholar (a) V. A. Ginsburg, L. L. Martynova, S. S. Dubov, B. I. Tetelbaum, and A. Y. Yakubovich, Zh. Obshch. Khim., 35, 851 (1965); Google Scholar Chem. Abstr., 63, 6995 (1965); Google Scholar(b) V. A. Ginsburg, S. S. Dubov, A. N. Medvedev, L. L. Martynova, B. I. Tetelbaum, M. N. Vasileva, and A. Y. Yakubovich, Dokl. Akad. Nauk SSSR, 152, 1104 (1963); CASWeb of Science®Google Scholar Chem. Abstr., 60, 1570 (1964). Google Scholar D. A. Barr and R. N. Haszeldine, J. Chem. Soc., 1881 (1955). Google Scholar N. Rieber, J. Alberts, J. A. Lipsky, and D. M. Lemal, J. Am. Chem. Soc., 91, 5668 (1969). 10.1021/ja01048a056 CASWeb of Science®Google Scholar M. E. Landis and J. C. Mitchell, J. Org. Chem., 44, 2288 (1979). 10.1021/jo01327a056 CASWeb of Science®Google Scholar M. Colonna and A. Risaliti, Gazz. Chim. Ital., 87, 923 (1957). CASGoogle Scholar M. Colonna and A. Risaliti, Gazz. Chim. Ital., 89, 2493 (1959). Google Scholar A. Risaliti and A. Monti, Gazz. Chim. Ital., 90, 397 (1960). CASGoogle Scholar A. R. Katritzki and S. Musierowicz, J. Chem. Soc. (C), 78 (1966). Google Scholar J. Markert and E. Fahr, Tetrahedron Lett., 4337 (1967). Google Scholar S. F. Nelson, V. E. Peacock, G. R. Weisman, M. E. Landis, and J. A. Spencer, J. Am. Chem. Soc., 100, 2806 (1978). 10.1021/ja00477a038 CASWeb of Science®Google Scholar C. W. Bird, J. Chem. Soc., 674 (1963). Google Scholar P. C. Freer, Am. Soc., 21, 14 (1899). Google Scholar D. Y. Curtin and E. W. Tristram, J. Am. Chem. Soc., 72, 5238 (1950). 10.1021/ja01167a126 CASWeb of Science®Google Scholar P. Singh, D. G. B. Boocock, and E. F. Ullman, Tetrahedron Lett., 3935 (1971). Google Scholar E. F. Ullman and P. Singh, J. Am. Chem. Soc., 94, 5077 (1972). 10.1021/ja00769a048 CASWeb of Science®Google Scholar (a) P. Singh and E. F. Ullman (Syva Corp.), U.S. Patent 3,953,444 (1976); Google Scholar Chem. Abstr., 85, 47641 (1976); Google Scholar (b) E. F. Ullman (Syva Corp.), U.S. Patent 4,032,519 (1977); Google Scholar Chem. Abstr., 87, 102306 (1977). Google Scholar F. D. Greene and K. E. Gilbert, J. Org. Chem., 40, 1409 (1975). 10.1021/jo00898a007 CASWeb of Science®Google Scholar L. B. Volodarskii and L. A. Tikhonova, Khim. Geterocycl. Soedin., 748 (1975). Google Scholar L. B. Volodarskii, L. A. Tikhonova, and S. A. Amitina, U.S.S.R. Patent 481,593 (1975); Google Scholar Chem. Abstr., 84, 31039 (1975). Google Scholar L. B. Volodarskii, L. A. Tikhonova, and S. A. Amitina, Izv. Akad. Nauk SSSR, Ser. Khim., 738 (1974); Google Scholar Chem. Abstr., 81, 3797 (1974). Google Scholar L. A. Tikhonova and L. B. Volodarskii, Ivz. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 103 (1977); Google Scholar Chem. Abstr., 87, 5844 (1977). Google Scholar W. J. Urry, P. Szecsi, C. Ikoku, and D. W. Moore, J. Am. Chem. Soc., 86, 2224 (1964). 10.1021/ja01065a024 CASWeb of Science®Google Scholar R. B. Greenwald and E. C. Taylor, J. Am. Chem. Soc., 90, 5272 (1968). 10.1021/ja01021a041 CASWeb of Science®Google Scholar P. C. Ip, K. Ramakrishnan, and J. Warkentin, Can. J. Chem., 52, 3671 (1974). 10.1139/v74-548 CASWeb of Science®Google Scholar T. H. Gorrie and N. F. Haley, J. Chem. Soc., Chem. Commun., 1081 (1972). Google Scholar C. J. Fritchie, Jr. and J. L. Wells, J. Chem. Soc., Chem. Commun., 917 (1968). Google Scholar R. B. Greenwald and E. C. Taylor, J. Am. Chem. Soc., 90, 5273 (1968). 10.1021/ja01021a042 CASWeb of Science®Google Scholar P. Grammaticakis, Compt. Rend. Hebd. Sci., 259, 2113 (1964). Web of Science®Google Scholar P. H. Ogden, J. Chem. Soc., Chem. Commun., 2920 (1971). Google Scholar A. B. Evnin, D. R. Arnold, L. A. Karnischky, and E. Strom, J. Am. Chem. Soc., 92, 6218 (1970). 10.1021/ja00724a021 CASWeb of Science®Google Scholar C. Calvo, P. C. Ip, N. Krishnamachari, and J. Warkentin, Can. J. Chem., 52, 2613 (1974). 10.1139/v74-381 CASWeb of Science®Google Scholar K. Oe, M. Tashiro, and O. Tsuge, Hukusokan Kagaku Toronkai Koen Yoshishu, 14 (1975); Google Scholar Chem. Abstr., 84, 164742 (1976). Google Scholar (a) R. Pfister and F. Häfliger (Geigy Chem. Corp.), U.S. Patent 2,859,211 (1958); Google Scholar Chem. Abstr., 53, 7196 (1959); Google Scholar (b) J. R. Geigy A.-G., Brit. Patent 813,474 (1959). Google Scholar A. Blade Font and J. M. Torres, Quim. Ind. (Madrid), 17, 110 (1971); Google Scholar Chem. Abstr., 75, 20277 (1971). Google Scholar F. Schatz, T. Wagner-Jauregg, and U. Jahn (Siegfried A.-G.), Swiss Patent 482,682 (1970); Google Scholar Chem. Abstr., 72, 90455 (1970); Google ScholarBrit. Patent 1,199,107 (1970); Google Scholar Chem. Abstr., 74, 13148 (1971). Google Scholar E. F. Ulman, L. Call, and S.S. Tseng, J. Am. Chem. Soc., 95, 1677 (1973). 10.1021/ja00786a063 Web of Science®Google Scholar Y. Huseya, A. Chinone, and M. Ohta, Bull. Chem. Soc. Japan, 45 3202 (1972). 10.1246/bcsj.45.3202 CASWeb of Science®Google Scholar P. G. Gassman, P. K. G. Hodgson, and R. J. Balchunis, J. Am. Chem. Soc., 98, 1275 (1976). 10.1021/ja00421a046 CASWeb of Science®Google Scholar A. S. Filatov, S. P. Makarov, and A. Y. Yakubovich, Zh. Obshch. Khim., 38, 1721 (1968); Google Scholar Chem. Abstr., 70, 3879 (1969). Google Scholar M. E. Landis, L. M. Bell, D. C. Madoux, J. C. Mitchell, J. M. Schmidt, and J. A. Spencer, J. Am. Chem. Soc., 102, 837 (1980). 10.1021/ja00522a066 CASWeb of Science®Google Scholar P. S. Engel, R. A. Hayes, L. Keifer, S. Szilagyi, and J. W. Timberlake, J. Am. Chem. Soc., 100, 1876 (1978). 10.1021/ja00474a037 CASWeb of Science®Google Scholar J. J. Cosa, H. E. Gsponer, E. H. Staricco, and C. A. Vallana, J. Chem. Soc. Faraday Trans. 1, 69, 1817 (1973). 10.1039/f19736901817 Web of Science®Google Scholar M. A. Englin, A. S. Filatov, and N. F. Alekseeva, Zh. Org. Khim., 7, 2611 (1971). Web of Science®Google Scholar J. L. Gerlock, E. G. Janzen, and J. K. Ruff, J. Am. Chem. Soc., 92, 2558 (1970). 10.1021/ja00711a065 CASWeb of Science®Google Scholar M. A. Englin, A. S. Filatov, and N. F. Alekseeva, Zh. Org. Khim., 7, 2319 (1971). Web of Science®Google Scholar L. Horner and E. Spietschka, Chem. Ber., 89, 2765 (1956). 10.1002/cber.19560891216 CASWeb of Science®Google Scholar J. H. Hall, J. Org. Chem., 29, 3188 (1964). 10.1021/jo01034a016 CASWeb of Science®Google Scholar E. Fahr and W. Fischer, Tetrahedron Lett., 3291 (1967). Google Scholar W. Fischer and E. Fahr, Angew. Chem. Int. Ed., 6, 630 (1967). 10.1002/anie.196706301 CASWeb of Science®Google Scholar G. Wittig, P. Börzel, F. Neumann, and G. Klar, Ann. Chem., 691, 109 (1965). 10.1002/jlac.19666910115 Web of Science®Google Scholar C. W. Bird, Chem. and Ind., 1556 (1963). Google Scholar C. W. Bird, J. Chem. Soc., Chem. Commun., 1486 (1969). Google Scholar S. S. Dubov and O. G. Strukov, Tr. Soveshch. Fis. Metod. Issled. Organ. Soedin. Khim. Protsessov, Akad Nauk Kirg. SSR, Inst. Organ. Khim., Frunze, 1962, p. 94; Google Scholar Chem. Abstr., 62, 4785 (1965). Google Scholar P. Ogden, J. Chem. Soc., Chem. Commun., 1084 (1969). Google Scholar E. Fahr, W. Rohlfing, R. Thiedemann, A. Mannschreck, G. Rissmann, and W. Seitz, Tetrahedron Lett., 3605 (1970). Google Scholar E. H. Carlson, A. P. Schaap, and M. Raban, J. Org. Chem., 38, 1605 (1973). 10.1021/jo00948a034 CASWeb of Science®Google Scholar A. Mannschreck, V. Jonas, and B. Kolb, Angew. Chem. Int. Ed., 12, 583 (1973). 10.1002/anie.197305831 Web of Science®Google Scholar P. Rademacher, Tetrahedron Lett., 83 (1974). Google Scholar P. Rademacher and H. Koopmann, Chem. Ber., 108, 1557 (1975). 10.1002/cber.19751080525 CASWeb of Science®Google Scholar K. E. Gilbert, J. Org. Chem., 42, 609 (1977). 10.1021/jo00424a006 CASWeb of Science®Google Scholar L. S. Domelsmith, K. N. Houk, J. W. Timberlake, and S. Szilagyi, Chem. Phys. Lett., 48, 471 (1977). 10.1016/0009-2614(77)85073-2 CASWeb of Science®Google Scholar F. Brogli, W. Eberbach, E. Haselbach, E. Heilbronner, V. Hornung, and D. M. Lemal, Helv. Chim. Acta, 56, 1933 (1973). Google Scholar H. Ruben, H. Bates, A. Zalkin, and D. H. Templeton, Acta Crystallogr., Sect. B, 30, 1631 (1974). 10.1107/S0567740874005462 Web of Science®Google Scholar Tollens and Hölzer, Chem. Ber., 17, 659 (1884). Google Scholar H. Schiff, Justus Liebigs Ann. Chem., 151, 206 (1869). 10.1002/jlac.18691510208 Google Scholar A. W. Hofmann, Jahresberichte, 349 (1858). Google Scholar H. Staudinger, Die Ketene, Enke, Stuttgart, 1912, p. 126. Google Scholar C. J. Brown, J. Chem. Soc., 2931 (1955). Google Scholar W. J. Hale, J. Am. Chem. Soc., 40, 370 (1918). 10.1021/ja02240a009 Google Scholar K. D. Petrov, E. S. Lagucheva, and V. I. Pukhova, Zh. Obshch. Khim., 23, 1771 (1953). Web of Science®Google Scholar H. D. Hartough, S. L. Meisel, E. Koft, and J. W. Shick, J. Am. Chem. Soc., 70, 4013 (1948). 10.1021/ja01192a013 CASPubMedWeb of Science®Google Scholar H. D. Hartough, J. W. Shick, and J. J. Dickert, Jr., J. Am. Chem. Soc., 72, 1572 (1950). 10.1021/ja01160a040 CASWeb of Science®Google Scholar (a) C. D. Wright and J. L. Zollinger, J. Org. Chem., 38, 1975 (1973); Google Scholar(b) H. W. Roesky and E. Janssen, Z. Naturforsch., 29b, 177 (1974). Google Scholar H. Ulrich, Acc. Chem. Res., 187 (1969). Google Scholar H. Ulrich, B. Tucker, and A. A. R. Sayigh, J. Am. Chem. Soc., 94, 3484 (1972). 10.1021/ja00765a039 CASWeb of Science®Google Scholar B. A. Arbuzov and N. N. Zobova, Synthesis, 461 (1974). Google Scholar R. Richter, Chem. Ber., 101, 174 (1968). 10.1002/cber.19681010122 CASWeb of Science®Google Scholar H. Helfert and E. Fahr, Angew. Chem. Int. Ed., 9, 372 (1970). 10.1002/anie.197003721 CASWeb of Science®Google Scholar (a) R. O. Kan and R. L. Furey, J. Am. Chem. Soc., 90, 1666 (1968); 10.1021/ja01008a057 CASWeb of Science®Google Scholar(b) C. K. Ingold and H. A. Piggott, J. Chem. Soc., 121, 2793 (1922). 10.1039/ct9222102793 CASWeb of Science®Google Scholar D. P. Deltsova, N. P. Gambaryan, Y. V. Zeifman, and I. L. Knunyants, Zh. Org. Khim., 8, 856 (1972). CASWeb of Science®Google Scholar N. P. Gambaryan and E. A. Avetisyan, Izv. Akad. Nauk SSSR, Ser. Khim., 358 (1976). Google Scholar F. Zetzsche and A. Fredrich, Ber., 73, 1114 (1940). 10.1002/cber.19400731016 Web of Science®Google Scholar K. Hartke, F. Rossbach, and M. Radau, Justus Liebigs Ann. Chem., 762, 167 (1972). 10.1002/jlac.19727620118 CASWeb of Science®Google Scholar A. V. Narbut and G. I. Derkach, Zh. Obshch. Khim., 39, 1698 (1969). CASGoogle Scholar L. Ruppert, Angew. Chem., 89, 336 (1977). 10.1002/ange.19770890522 CASGoogle Scholar H. L. Snape, J. Chem. Soc., 49, 254 (1886). 10.1039/ct8864900254 CASGoogle Scholar W. J. Balon and O. Stallmann, U.S. Patent 2,683,144 (1952); Google Scholar Chem. Abstr., 48, 12465 (1954). Google Scholar J. S. Blair and G. E. P. Smith, J. Am. Chem. Soc., 56, 907 (1934). 10.1021/ja01319a044 CASGoogle Scholar G. Oertel and H. Holtschmidt, U.S. Patent 3,290,288 (1966); Google Scholar Chem. Abstr., 67, 90788 (1967). Google Scholar W. H. Lookwood, FIAT Final Rept. No. 1301 (1947). Google Scholar H. J. Wild and F. E. G. Tate, U.S. Patent 3,144,452 (1964); Google Scholar Chem. Abstr., 61, 16068 (1964). Google Scholar J. M. Lyon and R. H. Thomson, J. Chem. Soc., 1971 (1950). Google Scholar S. Y. Han, T. J. Min, D. Y. Lee, and I. K. Lee, Daehan Hwahak Hwoejee, 15, 318 (1971); CASGoogle Scholar Chem. Abstr., 76, 140740 (1972). Google Scholar S. Y. Han, U. H. Paek, D. Y. Lee, and I. K. Lee, Daehan Hwahak Hwoejee, 17, 188 (1973); Google Scholar Chem. Abstr., 79, 78906 (1973). Google Scholar H. Ulrich, Cycloaddition Reactions of Heterocumulenes, Academic Press, New York, pp. 124–125. Google Scholar J. L. Bach, W. M. Beyleveld, and C. Woolf, NASA Accession No. N66–30268 Report No. AD631374 (1965); Google Scholar Chem. Abstr., 66, 32376 (1967). Google Scholar W. Frentzel, Chem. Ber., 21, 411 (1888). 10.1002/cber.18880210173 Google Scholar R. G. Arnold, J. A. Nelson, and J. J. Verbanc, Chem. Rev., 57, 47 (1957). 10.1021/cr50013a002 CASWeb of Science®Google Scholar Farbenfabriken Bayer A. G., Fr. Patent 1,532,054 (1968); Google Scholar Chem. Abstr., 71, 81328 (1969). Google Scholar N. Kuhn, W. Schwarz, and A. Schmidt, Chem. Ber., 110, 1130 (1977). 10.1002/cber.19771100335 CASWeb of Science®Google Scholar R. Richter and H. Ulrich, Synthesis, 463 (1975). Google Scholar L. C. Raiford and H. B. Freyermuth, J. Org. Chem., 8, 230 (1943). 10.1021/jo01191a004 CASWeb of Science®Google Scholar H. Gehlen and M. Just, Justus Liebigs Ann. Chem., 692, 151 (1966). 10.1002/jlac.19666920118 CASWeb of Science®Google Scholar E. S. Gubnitskaja and G. I. Derkach, Zh. Obshch. Khim., 42, 296 (1972). Web of Science®Google Scholar R. Richter and H. Ulrich, J. Org. Chem., 43, 3060 (1978). 10.1021/jo00409a029 CASWeb of Science®Google Scholar M. Kutz and W. Reichen, Tetrahedron Lett., 1433 (1978). Google Scholar O. Tsuge and R. Mizuguchi, Nippon Kagaku Zasshi, 86, 325 (1965); 10.1246/nikkashi1948.86.325 CASGoogle Scholar Chem. Abstr., 63, 4299 (1965). Google Scholar (a) O. Tsuge and R. Mizuguchi, Kogyo Kagaku Zasshi, 69, 939 (1966); 10.1246/nikkashi1898.69.5_939 CASGoogle Scholar Chem. Abstr., 66, 85552 (1967); Google Scholar(b) O. Tsuge and K. Sakai, Bull. Chem. Soc. Japan, 1534 (1972); Google Scholar Chem. Abstr., 77, 48411 (1972). Google Scholar G. Zinner and G. Isensee, Chem. Ztg., 97, 73 (1973). Web of Science®Google Scholar B. N. Kozhushko, A. V. Gumenyuk, and Y. A. Paliichuk, Zh. Obshch. Khim., 47, 333 (1977). Web of Science®Google Scholar E. Meisert and W. Altner, Germ. Patent 1,164,395 (1964); Google Scholar Chem. Abstr., 60, 14434 (1964). Google Scholar F. L. Kligman, M. I. Bakhitov, E. V. Kuznetsov, and S. L. Zainutdinova, Zh. Org. Khim., 12, 2026 (1976). CASWeb of Science®Google Scholar E. G. Tate and J. H. Wild, Brit. Patent 821,148 (1959); Google Scholar Chem. Abstr., 54, 14284 (1960). Google Scholar V. G. Sinyavskii and V. F. Kovaleva, Zh. Org. Khim., 5, 1888 (1969). Google Scholar M. Brown, U.S. Patent 3,214,412 (1965); Google Scholar Chem. Abstr., 64, 3542 (1966). Google Scholar N. P. Smetankina, N. I. Miryan, and V. E. Didkovskii, Zh. Obshch, Khim., 39, 2016 (1969). Google Scholar W. Gottardi and D. Henn, Mh. Chem., 100, 1860 (1969); CASWeb of Science®Google Scholar Mh. Chem., 101, 264 (1970). CASWeb of Science®Google Scholar G. Boden, W. Grosskreutz, G. Kessler, and H. Scheler, J. Chem., 12, 299 (1972). 10.1002/zfch.19720120815 Web of Science®Google Scholar A. Haas and H. Reinke, Chem. Ber., 102, 2718 (1969). 10.1002/cber.19691020830 CASWeb of Science®Google Scholar A. Haas, Chem. Ber., 98, 111 (1965). 10.1002/cber.19650980113 CASWeb of Science®Google Scholar A. Haas and Doug-Young Oh, Chem. Ber., 100, 480 (1967). 10.1002/cber.19671000214 CASWeb of Science®Google Scholar J. Goerdler and K. Jonas, Chem. Ber., 99, 3572 (1968). 10.1002/cber.19660991125 Web of Science®Google Scholar R. Hofmann, E. Schmidt, A. Reichle, and F. Moosmüller, Germ. Patent 1,012,601 (1957), Google Scholar Chem. Abstr., 53, 19892. (1959). Google Scholar W. J. Farrissey, Jr., R. J. Riccardi, and A. A. R. Sayigh, J. Org. Chem., 33, 1913 (1968). Google Scholar W. Neumann and P. Fischer, Angew. Chem. Int. Ed., 1, 621 (1962). 10.1002/anie.196206211 Google Scholar R. Neidlein, Arch. Pharm., 297, 623 (1964). 10.1002/ardp.19642971008 CASPubMedWeb of Science®Google Scholar H. Ulrich, B. Tucker, and A. A. R. Sayigh, J. Am. Chem. Soc., 90, 528 (1968). 10.1021/ja01004a079 CASWeb of Science®Google Scholar Y. I. Dergunov, A. S. Gordetsov, I. A. Vostokov, and V. A. Galperin, Zh. Obshch. Khim., 45, 2234 (1975). CASWeb of Science®Google Scholar H. Suschitzky, R. E. Walround, and R. Hull, J. Chem. Soc. Perkin I, 47 (1977). Google Scholar Y. I. Dergunov, A. S. Gordetsov, I. A. Vostokov, and V. F. Gerega, Zh. Obshch. Khim., 44, 2166 (1974). Web of Science®Google Scholar Y. I. Dergunov, A. S. Gordetsov, A. I. Vostokov, and V. F. Gerega, Zh. Obshch. Khim., 44, 1523 (1974). CASWeb of Science®Google Scholar Farbenfabriken Bayer A. G., Brit. Patent 959,997 (1964); Google Scholar Chem. Abstr., 61, 6924 (1964). Google Scholar R. Richter, Chem. Ber., 102, 938 (1969). 10.1002/cber.19691020328 CASWeb of Science®Google Scholar N. S. Kozlov, V. D. Pak, and N. A. Ivanov, Tr. Perm. Gos. Selskokhoz. Inst., 68, 149 (1970); CASGoogle Scholar Chem. Abstr., 77, 139856 (1972). Google Scholar J. Bödeker and K. Courault, Tetrahedron, 34, 101 (1978). 10.1016/0040-4020(78)88042-9 Web of Science®Google Scholar A. Senier and F. G. Shephard, J. Chem. Soc., 95, 494 (1909). 10.1039/ct9099500494 CASWeb of Science®Google Scholar N. N. Zobova, G. N. Rusanov, and B. A. Arbuzov, Izv. Akad. Nauk SSSR, Ser Khim., 2016 (1972). Google Scholar B. A. Arbuzov and N. N. Zobova, Izv. Akad. Nauk SSSR, Ser. Khim., 2607 (1973). Google Scholar B. A. Arbuzov, N. N. Zobova, and N. R. Rubinova, Izv. Akad. Nauk SSSR, Ser. Khim., 953 (1977). Google Scholar J. H. Sellstedt, D. M. Teller, and C. J. Guinosso, U.S. Patent 3,720,666 (1973); Google Scholar Chem. Abstr., 79, 5329 (1973). Google Scholar U. Kraatz, Tetrahedron Lett., 1219 (1973). Google Scholar G. Entenmann, Tetrahedron Lett., 3279 (1974). Google Scholar W. J. Hale and N. A. Lange, J. Am. Chem. Soc., 41, 379 (1919). 10.1021/ja01460a013 CASWeb of Science®Google Scholar G. Schwenker and R. Kolb, Tetrahedron, 25, 5437 (1969). 10.1016/S0040-4020(01)83045-3 CASPubMedWeb of Science®Google Scholar H. Ulrich, B. Tucker, and A. A. R. Sayigh, Angew. Chem. Int. Ed., 7, 291 (1968). 10.1002/anie.196802912 CASWeb of Science®Google Scholar G. Zinner and R. Vollrath, Chem. Ztg., 97, 38 (1973). CASWeb of Science®Google Scholar W. T. Flowers, R. Franklin, R. N. Haszeldine, and R. J. Perry, J. Chem. Soc., Chem. Commun., 567 (1976). Google Scholar G. Zinner and R. Vollrath, Z. Chem., 10, 30 (1970). 10.1002/zfch.19700100106 CASGoogle Scholar (a) K. H. Koenig, A. Fischer, and B. Zeeh, Germ. Offen. 2,027,345 (1971); Google Scholar Chem. Abstr., 76, 72500 (1972); Google Scholar (b) A. G. Jelinek, U.S. Patent 3,579,500 (1971); Google Scholar Chem. Abstr., 75, 35991 (1971). Google Scholar J. C. Stowell, F. D. Greene, and W. R. Bergmark, J. Org. Chem., 36, 3056 (1971). 10.1021/jo00819a039 CASWeb of Science®Google Scholar H. Ulrich, J. N. Tilley, and A.A. R, Sayigh, J. Org. Chem., 29, 2401 (1964). 10.1021/jo01031a072 CASWeb of Science®Google Scholar H. Ulrich and A. A. R. Sayigh, Angew. Chem. Int. Ed., 5, 704 (1966). 10.1002/anie.196607041 CASPubMedWeb of Science®Google Scholar D. K. White and F. D. Greene, J. Org. Chem., 43, 4530 (1978). 10.1021/jo00417a032 CASWeb of Science®Google Scholar H. Ulrich and A. A. R. Sayigh, J. Org. Chem., 28, 1427 (1963). 10.1021/jo01040a532 CASGoogle Scholar L. C. Raiford and R. J. Shelton, J. Org. Chem., 4, 207 (1939). 10.1021/jo01215a001 CASGoogle Scholar W. H. Warren and F. E. Wilson, Chem. Ber., 68, 957 (1935). 10.1002/cber.19350680543 Google Scholar C. Raiford and H. B. Freyermuth, J. Org. Chem., 8, 174 (1943). 10.1021/jo01190a009 CASGoogle Scholar H. Hoberg and J. Korff, Justus Liebigs Ann. Chem., 1111 (1978). Google Scholar E. Schaumann and E. Kausch, Justus Liebigs Ann. Chem., 1560 (1978). Google Scholar L. N. Markovskij and E. A. Stookalo, Phosphorus, 4, 237 (1974). Google Scholar M. M. Kremlev, A. D. Biba, N. A. Kirsanova, G. I. Derkach, E. V. Bryukhova, and G. K. Semin, Ukr. Khim. Zh., 37, 1026 (1971); CASWeb of Science®Google Scholar Chem. Abstr., 76, 14008 (1972). Google Scholar M. O. Lozinskii, A. F. Shivanyuk, and P. S. Pelkis, Dopov. Akad. Nauk Ukr. RSR, Ser. B, 30, 266 (1968); Google Scholar Chem. Abstr., 69, 59144 (1968). Google Scholar M. O. Lozinskii, A. F. Shivanyuk, and P. S. Pelkis, Khim. Geterotsikl. Soedin. Sb., 176 (1971); Google Scholar Chem. Abstr., 77, 114292 (1972). Google Scholar A. J. Downs and A. Haas, Spectrochim. Acta, Part A, 23, 1023 (1967). 10.1016/0584-8539(67)80026-6 Web of Science®Google Scholar J. L. Baudour, Y. Delugeard, and M. Sanquer, Acta Crystallogr., Sect. B, 30, 691 (1974). 10.1107/S0567740874003530 CASWeb of Science®Google Scholar R. Richter and H. Ulrich, unpublished results. Google Scholar M. W. Barker and R. H. Jones, J. Heterocyclic Chem., 9, 169 (1972). 10.1002/jhet.5570090136 CASWeb of Science®Google Scholar P. A. Argabright, Fr. Patent 1,582,371 (1969); Google Scholar Chem. Abstr., 73, 35410 (1970). Google Scholar R. Gompper and J. Stetter, Tetrahedron Lett., 233 (1973). Google Scholar R. Richter and H. Ulrich, Tetrahedron Lett., 1875 (1974). Google Scholar R. Richter, Tetrahedron Lett., 5037 (1968). Google Scholar A. W. Hofmann, Chem. Ber., 4, 246 (1871). 10.1002/cber.18710040189 Google Scholar D. E. Thurman and C. E. Moyer, Jr., J. Heterocyclic Chem., 9, 459 (1972). 10.1002/jhet.5570090252 CASGoogle Scholar A. Haas and P. Schott, Chem. Ber., 99, 3103 (1966). 10.1002/cber.19660991007 CASWeb of Science®Google Scholar P. Singh and J. L. Boivin, Can. J. Chem., 40, 935 (1962). 10.1139/v62-140 CASWeb of Science®Google Scholar C. B. Puchalski, Anal. Chem., 45, 787 (1973). 10.1021/ac60326a038 Web of Science®Google Scholar J. H. Saunders and E. E. Hardy, J. Am. Chem. Soc., 75, 5439 (1953). 10.1021/ja01117a524 CASWeb of Science®Google Scholar L. C. Raiford and H. B. Freyermuth, J. Org. Chem., 8, 230 (1943). 10.1021/jo01191a004 CASWeb of Science®Google Scholar N. G. Gaylord and J. H. Crowdle, Chem. Ind. (London), 145 (1955). Google Scholar P. Singh and J. L. Boivin, Can. J. Chem., 40, 2411 (1962). 10.1139/v62-366 CASWeb of Science®Google Scholar W. Siefken, Justus Liebigs Ann. Chem., 562, 75 (1949). 10.1002/jlac.19495620202 CASGoogle Scholar P. Müller, K. Wagner, R. Müller, and B. Quiring, Angew. Macrom. Chem., 65, 23 (1977). 10.1002/apmc.1977.050650102 Web of Science®Google Scholar Citing Literature Chemistry of Heterocyclic Compounds: Small Ring Heterocycles—Part 2, Volume 42 ReferencesRelatedInformation
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