Initiierung durch Bindungsbildung - ein Konzept für spontane Additionen und Polymerisationen von Alkenen
2006; Wiley; Volume: 95; Issue: 6 Linguagem: Alemão
10.1002/ange.19830950604
ISSN1521-3757
Autores Tópico(s)History and advancements in chemistry
ResumoAngewandte ChemieVolume 95, Issue 6 p. 448-464 Aufsatz Initiierung durch Bindungsbildung — ein Konzept für spontane Additionen und Polymerisationen von Alkenen Prof. Dr. H. K. Hall Jr., Prof. Dr. H. K. Hall Jr. Department of Chemistry, College of Arts and Sciences The University of Arizona Tucson, AZ 85721 (USA)Search for more papers by this author Prof. Dr. H. K. Hall Jr., Prof. Dr. H. K. Hall Jr. Department of Chemistry, College of Arts and Sciences The University of Arizona Tucson, AZ 85721 (USA)Search for more papers by this author First published: Juni 1983 https://doi.org/10.1002/ange.19830950604Citations: 19AboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Spontane Additionen und Polymerisationen von Alkenen unterschiedlicher Elektronendichte führen zu einer großen Vielfalt kleiner sowie hochpolymerer Moleküle. Als wesentliche Zwischenstufe werden Tetramethylene vorgeschlagen, d. h. Resonanzhybride 1,4-diradikalischer und zwitterionischer Grenzstrukturen. Ihre Eigenschaften werden durch die endständigen Substituenten bestimmt: Zwitterionischer Charakter wird durch starke Donoren am Carbeniumzentrum und starke Acceptoren am Carbanionzentrum begünstigt; diradikalischer Charakter wird durch Acceptorgruppen am Acceptorende sowie Aryl- und Vinylgruppen als Donoren begünstigt. Zwitterionische Tetramethylene initiieren ionische Homopolymerisation, diradikalische Tetramethylene leiten alternierende Copolymerisation ein. Somit steht eine extrem empfindliche Technik zur Entdeckung und Charakterisierung dieser Zwischenstufen zur Verfügung. Die Effekte der Donor- und Acceptorsubstituenten lassen sich in Form eines „Organischen Periodensystems”︁ anordnen, welches die Bereiche der mechanistischen Änderung deutlich aufzeigt und Vorhersagen ermöglicht. — Dieses vereinheitlichende Konzept der Initiierung durch Bindungsbildung wird auf spontane Additionen und Polymerisationen von Heteroatom-Acceptormolekülen und 7,7,8,8-tetrasubstituierten Chinodimethanen sowie von Verbindungen mit labilen σ-Bindungen, wie Halogene und Peroxide, ausgeweitet. Radikalionenpaare, Charge-Transfer-Komplexe und zufällige Verunreinigungen werden als wesentliche Initiatoren ausgeschlossen. References 1 R. Hoffmann, S. Swaminathan, B. G. Odell, R. Gleiter, J. Am. Chem. Soc. 92 (1970) 7091. 10.1021/ja00727a013 CASWeb of Science®Google Scholar 2 G. A. Segal, J. Am. Chem. Soc. 96 (1974) 7892. 10.1021/ja00833a009 CASWeb of Science®Google Scholar 3 W. A. Pryor, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 12 (1971) 49. CASGoogle Scholar 4 L. M. Stephenson, J. I. Brauman, J. Am. Chem. Soc. 93 (1971) 1988. 10.1021/ja00737a024 CASWeb of Science®Google Scholar 5 P. D. Bartlett, N. A. Porter, J. Am. Chem. Soc. 90 (1968) 5317. 10.1021/ja01021a073 CASWeb of Science®Google Scholar 6(a) J. S. Chikos, J. Org. Chem. 44 (1979) 780; 10.1021/jo01319a025 Web of Science®Google Scholar(b) P. B. Dervan, D. S. Santilli, J. Am. Chem. Soc. 102 (1980) 3863. 10.1021/ja00531a031 CASWeb of Science®Google Scholar 7 R. Huisgen, Acc. Chem. Res. 10 (1977) 199. 10.1021/ar50114a002 CASWeb of Science®Google Scholar 8 W. T. Borden, E. R. Davidson, J. Am. Chem. Soc. 102 (1980) 5409. 10.1021/ja00536a057 CASWeb of Science®Google Scholar 9(a) J. A. Berson in P. de Mayo: Rearrangements in Ground and Excited States, Academic Press, New York 1980, Vol. 1, S. 311; 10.1016/B978-0-12-481301-4.50011-5 Google Scholar(b) W. T. Borden, React. Intermed. 2 (1981) 175. CASGoogle Scholar 10 L. Salem, C. Rowland, Angew. Chem. 84 (1972) 86; 10.1002/ange.19720840303 Google Scholar Angew. Chem. Int. Ed. Engl. 11 (1972) 92. 10.1002/anie.197200921 CASWeb of Science®Google Scholar 11 R. Gompper, W. Elser, H. J. Müller, Angew. Chem. 79 (1967) 473; 10.1002/ange.19670791011 Google Scholar Angew. Chem. Int. Ed. Engl. 6 (1967) 453. Google Scholar 12 H. G. Viehe, R. Merenyi, L. Stella, Z. Janousek, Angew. Chem. 91 (1979) 982; 10.1002/ange.19790911206 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 18 (1979) 917. 10.1002/anie.197909171 Web of Science®Google Scholar 13 K. D. Gundermann, E. Roehrl, Justus Liebigs Ann. Chem. 1974, 1661. 10.1002/jlac.197419741017 Google Scholar 14 R. Huisgen, R. Schug, G. Steiner, Angew. Chem. 86 (1974) 47; 10.1002/ange.19740860111 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 13 (1974) 80. 10.1002/anie.197400801 Web of Science®Google Scholar 15 W. Weber, I. Erden, A. de Meijere, Angew. Chem. 92 (1980) 387; 10.1002/ange.19800920509 CASWeb of Science®Google Scholar Angew. Chem. Int. Ed. Engl. 19 (1980) 387. 10.1002/anie.198003871 CASWeb of Science®Google Scholar 16 J. K. Stille, N. Oguni, D. C. Chung, R. F. Tarvin, S. Aoki, M. Kamachi, J. Macromol. Sci. Chem. A9 (1975) 745. 10.1080/00222337508065892 CASWeb of Science®Google Scholar 17 R. F. Tarvin, S. Aoki, J. K. Stille, Macromolecules 5 (1972) 663. 10.1021/ma60030a001 CASWeb of Science®Google Scholar 18 F. Kataoka, N. Shimizu, S. Nishida, J. Am. Chem. Soc. 102 (1980) 711. 10.1021/ja00522a045 CASWeb of Science®Google Scholar 19 W. A. Pryor in W. A. Pryor: Organic Free Radicals, ACS Symp. Ser. 69 (1978) 33. 10.1021/bk-1978-0069.ch003 CASGoogle Scholar 20 A. T. Bottini, L. J. Cabral, V. Dev, Tetrahedron Lett. 1977, 615. Google Scholar 21 P. D. Bartlett, Q. Rev. Chem. Soc. 24 (1970) 473. 10.1039/qr9702400473 CASGoogle Scholar 22 R. Huisgen, Acc. Chem. Res. 10 (1977) 117. 10.1021/ar50112a003 CASWeb of Science®Google Scholar 23 T. Okuyama, M. Nakada, K. Toyoshima, T. Fueno, J. Org. Chem. 43 (1978) 4546. 10.1021/jo00417a041 CASWeb of Science®Google Scholar 24 Y. Shirota, H. Mikawa, J. Macromol. Sci. Rev. Macromol. Chem. C 16 (1977) 129. 10.1080/00222357608064317 Google Scholar 25 C. E. H. Bawn, A. Ledwith, M. Sambhi, Polymer 12 (1971) 209. 10.1016/0032-3861(71)90046-2 CASWeb of Science®Google Scholar 26 T. Nakamura, M. Soma, T. Onishi, K. Tamaru, Makromol. Chem. 135 (1970) 241. 10.1002/macp.1970.021350122 CASWeb of Science®Google Scholar 27 H. Graf, R. Huisgen, J. Org. Chem. 44 (1979) 2594, 2595. 10.1021/jo01328a064 CASWeb of Science®Google Scholar 28 S. Nishida, I. Moritani, T. Teraji, J. Org. Chem. 38 (1973) 1878. 10.1021/jo00950a021 CASWeb of Science®Google Scholar 29 J. K. Williams, D. W. Wiley, B. C. McKusick, J. Am. Chem. Soc. 84 (1962) 2210. 10.1021/ja00870a037 CASWeb of Science®Google Scholar 30 F. K. Fleischmann, H. Kelm, Tetrahedron Lett. 1973, 3773. Google Scholar 31 P. J. Wagner, K. C. Liu, Y. Noguchi, J. Am. Chem. Soc. 103 (1981) 3837. 10.1021/ja00403a035 CASWeb of Science®Google Scholar 32 T. Sasaki, K. Kanematsu, M. Uchide, Tetrahedron Lett. 1971, 4855. Google Scholar 33 W. Adam, O. DeLucchi, D. Scheutzow, J. Org. Chem. 46 (1981) 4130. 10.1021/jo00334a004 CASWeb of Science®Google Scholar 34 F. Kataoka, S. Nishida, Chem. Lett. 1980, 1115. Google Scholar 35 R. Gompper, Angew. Chem. 81 (1969) 348; 10.1002/ange.19690811003 Google Scholar Angew. Chem. Int. Ed. Engl. 8 (1969) 312. 10.1002/anie.196903121 CASWeb of Science®Google Scholar 36 S. Iwatsuki, Y. Yamashita, Adv. Polym. Sci. Jpn. 2 (1971) 1. CASGoogle Scholar 37 L. M. Quick, D. A. Knecht, M. H. Back, Int. J. Chem. Kinet. 4 (1972) 61. 10.1002/kin.550040105 CASGoogle Scholar 38 W. A. Pryor, L. D. Laswell, Adv. Free-Radical Chem. 5 (1975) 27. CASGoogle Scholar 39 W. A. Pryor, M. Iino, G. R. Newkome, J. Am. Chem. Soc. 99 (1977) 6003. 10.1021/ja00460a027 CASWeb of Science®Google Scholar 40 J. R. Lacher, G. W. Tompkin, J. D. Park, J. Am. Chem. Soc. 74 (1952) 1693. 10.1021/ja01127a024 CASWeb of Science®Google Scholar 41 W. H. Sharkey, Fluorine Chem. Rev. 2 (1968) 1. Google Scholar 42 A. L. Henne, R. P. Ruh, J. Am. Chem. Soc. 69 (1947) 279. 10.1021/ja01194a035 CASWeb of Science®Google Scholar 43 B. Atkinson, C. Tsiamis, Int. J. Chem. Kinet. 11 (1979) 585. 10.1002/kin.550110605 CASWeb of Science®Google Scholar 44 P. D. Bartlett, L. K. Montgomery, B. Seidel, J. Am. Chem. Soc. 86 (1964) 616. 10.1021/ja01058a016 CASWeb of Science®Google Scholar 45 L. K. Montgomery, K. Schueller, P. D. Bartlett, J. Am. Chem. Soc. 86 (1964) 622. 10.1021/ja01058a017 CASWeb of Science®Google Scholar 46 I. Fleming, M. H. Karger, J. Chem. Soc. C 1967, 226. Google Scholar 47 M. Stickler, G. Meyerhoff, Polymer 22 (1981) 928. 10.1016/0032-3861(81)90270-6 CASWeb of Science®Google Scholar 48 C. J. Albisetti, D. C. England, M. J. Hogsed, R. M. Joyce, J. Am. Chem. Soc. 78 (1956) 472. 10.1021/ja01583a060 CASWeb of Science®Google Scholar 49 M. Stickler, G. Meyerhoff, Makromol. Chem. 181 (1980) 131, 913. 10.1002/macp.1980.021810113 CASWeb of Science®Google Scholar 50 C. Walling, J. Am. Chem. Soc. 71 (1949) 1930. 10.1021/ja01174a009 CASWeb of Science®Google Scholar 51 H. Inoue, T. Otsu, Makromol. Chem. 153 (1972) 21. 10.1002/macp.1972.021530103 CASWeb of Science®Google Scholar 52 L. P. Ellinger, Polymer 5 (1964) 559. 10.1016/0032-3861(64)90207-1 CASWeb of Science®Google Scholar 53 K. Nagai, S. Machida, T. Nonaka, J. Polym. Sci. Polym. Chem. Ed. 19 (1981) 773. 10.1002/pol.1981.170190316 CASWeb of Science®Google Scholar 54 K. Nagai, S. Machida, J. Macromol. Sci. Chem. A 16 (1981) 965. 10.1080/00222338108056453 Web of Science®Google Scholar 55 K. C. Brannock, R. D. Burpitt, J. G. Thweatt, J. Org. Chem. 29 (1964) 940. 10.1021/jo01027a502 CASWeb of Science®Google Scholar 56 K. C. Brannock, A. Bell, R. D. Burpitt, C. A. Kelly, J. Org. Chem. 26 (1961) 625; 10.1021/jo01061a074 CASWeb of Science®Google Scholar J. Org. Chem. 29 (1964) 801, 813. 10.1021/jo01027a009 CASWeb of Science®Google Scholar 57 I. Fleming, J. Harley-Mason, J. Chem. Soc. 1964, 2165. Google Scholar 58 C. Walling, E. A. McElhill, J. Am. Chem. Soc. 73 (1951) 2819. 10.1021/ja01150a114 CASWeb of Science®Google Scholar 59 T. Sato, M. Abe, T. Otsu, J. Macromol. Sci. Chem. A 15 (1981) 367. 10.1080/00222338108074377 Web of Science®Google Scholar 60 F. D. Lewis, T. I. Ho, R. J. De Voe, J. Org. Chem. 45 (1980) 5283. 10.1021/jo01314a011 CASWeb of Science®Google Scholar 61 H. K. Hall, Jr., Y. Okamoto, A. B. Padias, A. Deutschman, Jr., J. W. Berry, J. Polym. Sci. Polym. Chem. Ed. 17 (1979) 3889. 10.1002/pol.1979.170171209 CASWeb of Science®Google Scholar 62 A. L. Barney, T. L. Cairns, J. Am. Chem. Soc. 72 (1950) 3193. 10.1021/ja01163a108 CASWeb of Science®Google Scholar 63 E. C. Coyner, W. S. Hillman, J. Am. Chem. Soc. 71 (1949) 324. 10.1021/ja01169a091 CASWeb of Science®Google Scholar 64 H. K. Hall, Jr., C. D. Smith, D. E. Plorde, J. Org. Chem. 38 (1973) 2084. 10.1021/jo00951a024 CASWeb of Science®Google Scholar 65 K. Kirchner, H. Schlapkohl, Makromol. Chem. 177 (1976) 2031. 10.1002/macp.1976.021770711 CASWeb of Science®Google Scholar 66 S. Tazuke, S. Okamura, J. Polym. Sci. A-1 6 (1968) 2907. 10.1002/pol.1968.150061018 CASWeb of Science®Google Scholar 67 R. W. Hoffmann, U. Bressel, J. Gehlhaus, H. Häuser, Chem. Ber. 104 (1971) 873. 10.1002/cber.19711040324 CASWeb of Science®Google Scholar 68 Th. Wagner-Jauregg, Synthesis 1980, 769. 10.1055/s-1980-29206 Google Scholar 69 M. Matsuda, K. Abe, J. Polym. Sci. A-1 6 (1968) 1441. 10.1002/pol.1968.150060603 Web of Science®Google Scholar 70 T. Sato, M. Abe, T. Otsu, Makromol. Chem. 178 (1977) 1061. 10.1002/macp.1977.021780411 CASWeb of Science®Google Scholar 71 M. Raetzsch, R. Hoyer, M. Arnold, Acta Polym. 31 (1980) 572. 10.1002/actp.1980.010310908 CASGoogle Scholar 72 Th. Wagner-Jauregg, Ber. Dtsch. Chem. Ges. 63 (1930) 3213. 10.1002/cber.19300631140 Web of Science®Google Scholar 73 T. Kokubo, S. Iwatsuki, Y. Yamashita, Makromol. Chem. 123 (1969) 256. 10.1002/macp.1969.021230124 CASWeb of Science®Google Scholar 74 T. Kokubo, S. Iwatsuki, Y. Yamashita, Macromolecules 1 (1968) 482. 10.1021/ma60006a005 CASGoogle Scholar 75 S. Iwatsuki, Y. Yamashita, Makromol. Chem. 89 (1965) 205. 10.1002/macp.1965.020890115 CASWeb of Science®Google Scholar 76 S. M. McElvain, H. Cohen, J. Am. Chem. Soc. 64 (1942) 260. 10.1021/ja01254a016 CASWeb of Science®Google Scholar 77 T. Otsu, H. Inoue, Makromol. Chem. 128 (1969) 31. 10.1002/macp.1969.021280103 CASWeb of Science®Google Scholar 78 N. Kushibiki, M. Irie, K. Hayashi, J. Polym. Sci. Polym. Chem. Ed. 13 (1975) 77. 10.1002/pol.1975.170130108 CASWeb of Science®Google Scholar 79 M. E. Kuehne, L. Foley, J. Org. Chem. 30 (1965) 4280. 10.1021/jo01023a066 CASWeb of Science®Google Scholar 80 H. K. Hall, Jr., R. C. Sentman, J. Org. Chem. 47 (1982) 4572. 10.1021/jo00144a033 CASWeb of Science®Google Scholar 81 H. K. Hall, Jr., M. Abdelkader, J. Org. Chem. 46 (1981) 2948. 10.1021/jo00327a022 CASWeb of Science®Google Scholar 82 H. K. Hall, Jr., H. A. A. Rasoul, M. Gillard, M. Abdelkader, P. Nogues, R. C. Sentman, Tetrahedron Lett. 23 (1982) 603. 10.1016/S0040-4039(00)86901-4 CASWeb of Science®Google Scholar 83 H. K. Hall, Jr., H. Tanaka, unveröffentlicht. Google Scholar 84 J. K. Hall, Jr., P. Ykman, J. Am. Chem. Soc. 97 (1975) 800. 10.1021/ja00837a020 CASWeb of Science®Google Scholar 85 M. Abdelkader, H. K. Hall, Jr., J. Org. Chem. 47 (1982) 292. 10.1021/jo00341a022 CASWeb of Science®Google Scholar 86 H. K. Hall, Jr., L. C. Dunn, A. B. Padias, J. Org. Chem. 45 (1980) 835. 10.1021/jo01293a015 CASWeb of Science®Google Scholar 87 H. K. Hall, Jr., M. Abdelkader, M. E. Glogowski, J. Org. Chem. 47 (1982) 6391. Google Scholar 88 M. E. Glogowski, H. K. Hall, Jr., J. Macromol. Sci. Chem. A 13 (1979) 369. 10.1080/00222337908068108 Web of Science®Google Scholar 89 R. C. Sentman, Ph. D. Thesis, University of Arizona 1982. Google Scholar 90 H. K. Hall, Jr., unveröffentlicht. Google Scholar 91 H. K. Hall, Jr., P. Nogues, J. W. Rhoades, R. C. Sentman, M. Detar, J. Org. Chem. 47 (1982) 1451. 10.1021/jo00347a014 CASWeb of Science®Google Scholar 92 P. H. J. Ooms, R. P. Bos, J. W. Scheeren, R. J. F. Nivard, J. Chem. Soc. Perkin Trans. I 1976, 1538. Google Scholar 93 P. H. J. Ooms, R. P. Bos, J. W. Schèeren, R. J. F. Nivard, Recl. J. R. Netherl. Chem. Soc. 96 (1977) 75. CASWeb of Science®Google Scholar 94 T. Otsu, B. Yamada, S. Kusayama, S. Nagao, Kobunshi Ronbunshu 36 (1979) 797; 10.1295/koron.36.797 CASWeb of Science®Google Scholar Chem. Abstr. 92 (1979) 94753 x. Google Scholar 95 H. A. A. Rasoul, H. K. Hall, Jr., J. Org. Chem. 47 (1982) 2080. 10.1021/jo00132a019 CASWeb of Science®Google Scholar 96 J. B. Kinsinger, J. R. Panchak, R. L. Kelso, J. S. Bartlett, R. K. Graham, J. Appl. Polym. Sci. 9 (1965) 429. 10.1002/app.1965.070090204 CASWeb of Science®Google Scholar 97 H. K. Hall, Jr., R. C. Daly, Macromolecules 8 (1975) 22. 10.1021/ma60043a006 CASWeb of Science®Google Scholar 98 H. K. Hall, Jr., K. Reineke, J. H. Ried, R. C. Sentman, D. Miller, J. Polym. Sci. Polym. Chem. Ed. 20 (1982) 361. 10.1002/pol.1982.170200210 CASWeb of Science®Google Scholar 99 S. Proskow, H. E. Simmons, T. L. Cairns, J. Am. Chem. Soc. 88 (1966) 5254. 10.1021/ja00974a041 CASWeb of Science®Google Scholar 100 J. P. Ortega, Mem. R. Acad. Cienc. Exactas Fis. Nat., Madrid, Ser. Cienc. Fis.-Quim. 9 (1979) 7; Google Scholar Chem. Abstr. 93 (1980) 45498 e. Google Scholar 101 J. Bitter, J. Leitich, H. Partale, O. E. Polansky, W. Riemer, U. Ritter-Thomas, B. Schlamann, B. Stilkerieg, Chem. Ber. 113 (1980) 1020. 10.1002/cber.19801130321 CASWeb of Science®Google Scholar 102 P. H. J. Ooms, J. W. Scheeren, R. J. F. Nivard, Synthesis 1975, 260, 263. 10.1055/s-1975-23724 Google Scholar 103 H. Gilbert, F. F. Miller, S. J. Averill, E. J. Carlson, V. L. Folt, H. J. Heller, F. D. Stewart, R. F. Schmidt, H. L. Trumbull, J. Am. Chem. Soc. 78 (1956) 1669. 10.1021/ja01589a049 CASWeb of Science®Google Scholar 104 J. K. Stille, D. C. Chung, Macromolecules 8 (1975) 83. 10.1021/ma60043a020 CASWeb of Science®Google Scholar 105 J. K. Stille, D. C. Chung, Macromolecules 8 (1975) 114. 10.1021/ma60044a005 CASWeb of Science®Google Scholar 106 J. K. Williams, D. W. Wiley, B. C. McKusick, J. Am. Chem. Soc. 84 (1962) 2216. 10.1021/ja00870a038 CASWeb of Science®Google Scholar 107 W. J. Middleton, J. Org. Chem. 30 (1965) 1402. 10.1021/jo01016a013 CASWeb of Science®Google Scholar 108 A. T. Blomquist, Y. C. Meinwald, J. Am. Chem. Soc. 81 (1959) 667. 10.1021/ja01512a040 CASWeb of Science®Google Scholar 109 S. Sarel, A. Felzenstein, J. Yovell, J. Chem. Soc. Chem. Commun. 1973, 859. Google Scholar 110 C. Ruecker, D. Lang, J. Sauer, H. Friege, R. Sustmann, Chem. Ber. 113 (1980) 1663. 10.1002/cber.19801130505 CASWeb of Science®Google Scholar 111 E. Ciganek, W. J. Linn, O. W. Webster in Z. Rappoport: The Chemistry of the Cyano Group, Interscience, New York 1970, S. 423. 10.1002/9780470771242.ch9 Google Scholar 112 F. Effenberger, O. Gerlach, Chem. Ber. 107 (1974) 278. 10.1002/cber.19741070134 CASWeb of Science®Google Scholar 113 M. Nakahara, Y. Uosaki, M. Sasaki, J. Osugi, Rev. Phys. Chem. Jpn. 47 (1977) 119. CASWeb of Science®Google Scholar 114 M. Sasaki, H. Tsuzuki, J. Osugi, J. Chem. Soc. Perkin Trans. II 1980, 1596. Google Scholar 115 J. von Jouanne, H. Kelm, R. Huisgen, J. Am. Chem. Soc. 101 (1979) 151. 10.1021/ja00495a026 CASWeb of Science®Google Scholar 116 T. Arimoto, J. Osugi, Chem. Lett. 1974, 271. Google Scholar 117 D. Masilamani, M. E. Reumann, M. M. Rogic, J. Org. Chem. 45 (1980) 4602. 10.1021/jo01311a010 CASWeb of Science®Google Scholar 118 H. Noguchi, S. Kambara, J. Polym. Sci. B 3 (1965) 271. 10.1002/pol.1965.110030406 CASWeb of Science®Google Scholar 119 S. Fries, K. Gollnick, Angew. Chem. 92 (1980) 848; 10.1002/ange.19800921020 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 19 (1980) 831. 10.1002/anie.198008311 Web of Science®Google Scholar 120 C. Hubschwerlen, J. P. Fleury, H. Fritz, Helv. Chim. Acta 60 (1977) 2576. 10.1002/hlca.19770600811 CASWeb of Science®Google Scholar 121 N. Wiberg, J. W. Buchler, Chem. Ber. 96 (1963) 3223. 10.1002/cber.19630961218 CASWeb of Science®Google Scholar 122 J. Lingnau, M. Stickler, G. Meyerhoff, Eur. Polym. J. 16 (1980) 785. 10.1016/0014-3057(80)90050-6 CASWeb of Science®Google Scholar 123 N. J. Barr, W. I. Bengough, G. Beveridge, G. B. Park, Eur. Polym. J. 14 (1978) 245. 10.1016/0014-3057(78)90044-7 CASWeb of Science®Google Scholar 124 H. K. Hall, Jr., H. A. A. Rasoul, M. Gillard, noch unveröffentlicht. Google Scholar 125 B. T. Gillis, J. D. Hagarty, J. Org. Chem. 32 (1967) 330. 10.1021/jo01288a016 CASWeb of Science®Google Scholar 126 R. L. Adelman, J. Org. Chem. 33 (1968) 1400. 10.1021/jo01268a600 CASWeb of Science®Google Scholar 127 D. C. England, C. G. Krespan, J. Org. Chem. 35 (1970) 3312. 10.1021/jo00835a029 CASWeb of Science®Google Scholar 128 O. Achmatowicz, Jr., J. Szymomiak, J. Org. Chem. 45 (1980) 4774. 10.1021/jo01311a046 CASWeb of Science®Google Scholar 129 W. A. Thaler, B. Franzus, J. Org. Chem. 29 (1964) 2226. 10.1021/jo01031a029 CASWeb of Science®Google Scholar 130 B. T. Gillis, P. E. Beck, J. Org. Chem. 28 (1963) 3177. 10.1021/jo01046a054 CASWeb of Science®Google Scholar 131 R. Huisgen, H. Pohl, Chem. Ber. 93 (1960) 527. 10.1002/cber.19600930242 CASWeb of Science®Google Scholar 132 E. Körner von Gustorf, D. V. White, B. Kim, D. Hess, J. Leitich, J. Org. Chem. 35 (1970) 1155. 10.1021/jo00829a065 CASWeb of Science®Google Scholar 133 J. H. Hall, M. Wojciechowska, J. Org. Chem. 43 (1978) 3348. 10.1021/jo00411a019 CASWeb of Science®Google Scholar 134 R. W. Hoffmann, U. Bressel, J. Gehlhaus, H. Hauser, Chem. Ber. 104 (1971) 873. 10.1002/cber.19711040324 CASWeb of Science®Google Scholar 135 S. R. Turner, M. Stolka, J. Polym. Sci. Polym. Chem. Ed. 16 (1978) 1167. 10.1002/pol.1978.170160526 CASWeb of Science®Google Scholar 136 S. Ohashi, K. Leong, K. Matyjaszewski, G. B. Butler, J. Org. Chem. 45 (1980) 3467. 10.1021/jo01305a020 CASWeb of Science®Google Scholar 137 S. Ohashi, G. B. Butler, J. Org. Chem. 45 (1980) 3472. 10.1021/jo01305a021 CASWeb of Science®Google Scholar 138 D. J. Pasto, A. F. T. Chen, Tetrahedron Lett. 1973, 713. Google Scholar 139 K. B. Wagener, S. R. Turner, G. B. Butler, J. Polym. Sci. Polym. Lett. Ed. 10 (1972) 805. 10.1002/pol.1972.130101009 CASWeb of Science®Google Scholar 140 K. B. Wagener, S. R. Turner, G. B. Butler, J. Org. Chem. 37 (1972) 1454. 10.1021/jo00974a042 CASWeb of Science®Google Scholar 141 K. B. Wagener, G. B. Butler, J. Org. Chem. 38 (1973) 3070. 10.1021/jo00957a042 CASWeb of Science®Google Scholar 142 G. B. Butler, L. J. Guilbault, S. R. Turner, J. Polym. Sci. Polym. Lett. Ed. 9 (1971) 115. 10.1002/pol.1971.110090208 CASWeb of Science®Google Scholar 143 L. J. Guilbault, S. R. Turner, G. B. Butler, J. Polym. Sci. Polym. Lett. Ed. 10 (1972) 1. 10.1002/pol.1972.110100101 CASWeb of Science®Google Scholar 144 L. J. Guilbault, S. R. Turner, G. B. Butler, Polym. Prepr., Am. Chem. Soc. Div. Polym. Chem. 13 (1972) 936. Google Scholar 145 M. E. Kuehne, P. J. Sheeran, J. Org. Chem. 33 (1968) 4406. 10.1021/jo01276a021 CASWeb of Science®Google Scholar 146 M. Delaunois, L. Ghosez, Angew. Chem. 81 (1969) 33; 10.1002/ange.19690810107 Google Scholar Angew. Chem. Int. Ed. Engl. 8 (1969) 72. 10.1002/anie.196900721 CASGoogle Scholar 147 D. C. England, C. G. Krespan, J. Am. Chem. Soc. 87 (1965) 4019. 10.1021/ja01095a066 CASWeb of Science®Google Scholar 148 R. T. Arnold, P. Veezagu, J. Am. Chem. Soc. 82 (1960) 5411. 10.1021/ja01505a029 CASWeb of Science®Google Scholar 149 P. H. J. Ooms, H. W. Scheeren, R. J. F. Nivard, J. Chem. Soc. Perkin Trans. I 1976, 1048. Google Scholar 150 O. Achmatowicz, F. Werner-Zamojska, Bull. Acad. Pol. Sci. Cl. Troisieme 5 (1957) 923; CASGoogle Scholar Chem. Abstr. 52 (1958) 6333. Google Scholar 151 O. Achmatowicz, M. Leplawy, A. Zamojski, Rocz. Chem. 30 (1956) 215; CASGoogle Scholar Chem. Abstr. 51 (1957) 1087. Google Scholar 152 R. Graf, Angew. Chem. 80 (1968) 179; 10.1002/ange.19680800503 Google Scholar Angew. Chem. Int. Ed. Engl. 7 (1968) 172. 10.1002/anie.196801721 CASWeb of Science®Google Scholar 153 L. A. Errede, M. Szwarc, Q. Rev. Chem. Soc. 12 (1958) 301. 10.1039/qr9581200301 CASWeb of Science®Google Scholar 154 S. Iwatsuki, H. Kamiya, Macromolecules 7 (1974) 732. 10.1021/ma60042a006 CASWeb of Science®Google Scholar 155 S. Iwatsuki, K. Inoue, Macromolecules 10 (1977) 58. 10.1021/ma60055a010 CASWeb of Science®Google Scholar 156 S. Iwatsuki, T. Itoh, Macromolecules 13 (1980) 983. 10.1021/ma60076a043 CASWeb of Science®Google Scholar 157 S. Iwatsuki, T. Itoh, K. Horiuchi, Macromolecules 11 (1978) 497. 10.1021/ma60063a014 CASWeb of Science®Google Scholar 158 S. Iwatsuki, T. Itoh, S. Sadaiki, Macromolecules 14 (1981) 1608. 10.1021/ma50006a098 CASWeb of Science®Google Scholar 159 S. Iwatsuki, T. Itoh, Macromolecules 12 (1979) 208. 10.1021/ma60068a008 CASWeb of Science®Google Scholar 160 S. Aoki, J. K. Stille, Macromolecules 3 (1970) 473. 10.1021/ma60016a021 CASWeb of Science®Google Scholar 161 H. Noguchi, S. Kambara, J. Polym. Sci. B 3 (1965) 271. 10.1002/pol.1965.110030406 CASWeb of Science®Google Scholar 162 H. Scott, G. A. Miller, M. M. Labes, Tetrahedron Lett. 1963, 1073. Google Scholar 163 S. Iwatsuki, T. Itoh, Macromolecules 15 (1982) 347. 10.1021/ma00230a029 CASWeb of Science®Google Scholar 164 T. Natsuume, M. Nishimura, M. Fujimatsu, M. Shimizu, Y. Shirota, H. Mikawa, Polym. J. Jpn. 1 (1970) 181. 10.1295/polymj.1.181 CASGoogle Scholar 165 S. Iwatsuki, T. Itoh, J. Polym. Sci. Polym. Chem. Ed. 18 (1980) 2971. 10.1002/pol.1980.170181007 CASWeb of Science®Google Scholar 166 J. A. K. Harmony, Methods Free Radical Chem. 5 (1974) 101. CASGoogle Scholar 167 M. Poutsma, Science 157 (1967) 997. 10.1126/science.157.3792.997 CASPubMedWeb of Science®Google Scholar 168 G. Belluci, G. Berti, R. Bianchini, G. Ingrosso, R. Ambrosetti, J. Am. Chem. Soc. 102 (1980) 7480. 10.1021/ja00545a014 Web of Science®Google Scholar 169 G. Fraenkel, P. D. Bartlett, J. Am. Chem. Soc. 81 (1959) 5582. 10.1021/ja01530a017 CASWeb of Science®Google Scholar 170 W. T. Miller, S. D. Koch, Jr., F. W. McLafferty, J. Am. Chem. Soc. 78 (1956) 4992. 10.1021/ja01600a050 CASWeb of Science®Google Scholar 171 F. D. Greene, W. W. Rees, J. Am. Chem. Soc. 80 (1958) 3432. 10.1021/ja01546a058 CASWeb of Science®Google Scholar 172 J. C. Bevington, C. J. Dyball, Polymer 17 (1976) 742. 10.1016/0032-3861(76)90223-8 CASWeb of Science®Google Scholar 173 J. C. Bevington, C. J. Dyball, Polymer 16 (1975) 938. 10.1016/0032-3861(75)90220-7 CASWeb of Science®Google Scholar 174 J. C. Bevington, C. J. Dyball, J. Chem. Soc. Faraday Trans. II 1975, 2226. Google Scholar 175 T. Sato, M. Abe, T. Otsu, Makromol. Chem. 178 (1977) 1259. 10.1002/macp.1977.021780504 CASWeb of Science®Google Scholar 176 F. R. Mayo, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2 (1961) 55. Google Scholar 177 K. Buchholz, K. Kirchner, Makromol. Chem. 177 (1976) 935. 10.1002/macp.1976.021770330 CASWeb of Science®Google Scholar 178 W. A. Pryor, R. A. Patsiga, Spectrosc. Lett. 2 (1969) 61, 353. 10.1080/00387016908050016 CASWeb of Science®Google Scholar 179 M. D. Shalati, R. M. Scott, Macromolecules 8 (1975) 127. 10.1021/ma60044a007 CASWeb of Science®Google Scholar 180 K. Yamasaki, T. Yonezawa, M. Ohashi, J. Chem. Soc. Perkin Trans. I 1975, 93. Google Scholar 181 K. Yamasaki, zitiert von S. Inagaki, H. Fujimoto, K. Fukui, J. Am. Chem. Soc. 97 (1975) 6108. 10.1021/ja00854a025 Web of Science®Google Scholar 182 E. A. Braude, L. M. Jackman, R. P. Linstead, J. Chem. Soc. 1954, 3548. Google Scholar 183 M. L. Poutsma, J. Am. Chem. Soc. 87 (1965) 2161. 10.1021/ja01088a014 CASWeb of Science®Google Scholar 184 M. L. Poutsma, J. Org. Chem. 31 (1966) 4167. 10.1021/jo01350a068 CASWeb of Science®Google Scholar 185 M. L. Poutsma, J. Am. Chem. Soc. 87 (1965) 2172. 10.1021/ja01088a015 CASWeb of Science®Google Scholar 186 C. Walling, L. Heaton, D. D. Tanner, J. Am. Chem. Soc. 87 (1965) 1715. 10.1021/ja01086a017 CASWeb of Science®Google Scholar 187 F. D. Greene, W. Adam, J. E. Cantrill, J. Am. Chem. Soc. 83 (1961) 3461. 10.1021/ja01477a027 CASWeb of Science®Google Scholar 188 F. D. Greene, J. Am. Chem. Soc. 78 (1956) 2250. 10.1021/ja01591a061 CASWeb of Science®Google Scholar 189 J. C. Martin, J. W. Taylor, E. H. Drew, J. Am. Chem. Soc. 89 (1967) 129. 10.1021/ja00977a025 CASWeb of Science®Google Scholar 190 C. Walling, Y. Chang, J. Am. Chem. Soc. 76 (1954) 4878. 10.1021/ja01648a036 CASWeb of Science®Google Scholar 191 D. Swern, J. Am. Chem. Soc. 69 (1947) 1692. 10.1021/ja01199a037 CASWeb of Science®Google Scholar 192 W. A. Thaler, B. Franzus, J. Org. Chem. 29 (1964) 2226. 10.1021/jo01031a029 CASWeb of Science®Google Scholar 193 H. K. Hall, Jr., J. Chem. Educ. 57 (1980) 49. 10.1021/ed057p49 CASWeb of Science®Google Scholar 194 V. Gutmann: The Donor-Acceptor Approach to Molecular Interactions, Plenum Press, New York 1978. 10.1007/978-1-4615-8825-2 Google Scholar 195 N. Oguni, M. Kamachi, J. K. Stille, Macromolecules 7 (1974) 435. 10.1021/ma60040a008 CASWeb of Science®Google Scholar 196 A. Ledwith, G. Galli, E. Chiellini, R. Solaro, Polym. Bull. 1 (1979) 491. 10.1007/BF00255714 CASWeb of Science®Google Scholar 197 G. Burillo, A. Chapiro, Z. Mankowski, J. Polym. Sci. Polym. Chem. Ed. 18 (1980) 327. 10.1002/pol.1980.170180131 CASWeb of Science®Google Scholar 198 H. A. A. Rasoul, H. K. Hall, Jr.: Proc. US-Japan Polymer Meetings, Palm Springs 1980, Marcel Dekker, New York, im Druck. Google Scholar 199 T. Saegusa, Angew. Chem. 89 (1977) 867; 10.1002/ange.19770891206 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 16 (1977) 826. 10.1002/anie.197708261 Web of Science®Google Scholar 200 R. B. Woodward, R. Hoffmann: Die Erhaltung der Orbitalsymmetrie, Verlag Chemie, Weinheim 1970; Google Scholar Angew. Chem. 81 (1969) 797; 10.1002/ange.19690812102 Web of Science®Google Scholar Angew. Chem. Int. Ed. Engl. 8 (1969) 781. 10.1002/anie.196907811 CASWeb of Science®Google Scholar 201 K. Fukui in: Reactivity and Structure Concepts in Organic Chemistry, Springer, Berlin 1978, Vol. 2. Google Scholar 202 T. L. Gilchrist, R. C. Storr: Organic Reactions and Orbital Symmetry, Cambridge University Press, Cambridge 1979. Google Scholar 203 J. Sauer, R. Sustmann, Angew. Chem. 92 (1980) 773; 10.1002/ange.19800921004 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 19 (1980) 779. 10.1002/anie.198007791 Web of Science®Google Scholar 204 K. N. Houk in A. P. Marchand, R. E. Lehr: Pericyclic Reactions, Academic Press, New York 1977, Vol. 2, S. 181. 10.1016/B978-0-12-470502-9.50010-9 Google Scholar 205 C. A. Stewart, J. Am. Chem. Soc. 84 (1962) 117. 10.1021/ja00860a032 CASWeb of Science®Google Scholar 206 J. C. Little, J. Am. Chem. Soc. 87 (1965) 4020. 10.1021/ja01095a068 CASWeb of Science®Google Scholar 207 J. J. Eisch, G. R. Husk, J. Org. Chem. 31 (1966) 589. 10.1021/jo01340a505 CASWeb of Science®Google Scholar 208 W. C. Herndon, J. Feuer, J. Org. Chem. 33 (1968) 417. 10.1021/jo01265a087 CASWeb of Science®Google Scholar 209 R. A. Firestone, Tetrahedron 33 (1977) 3009. 10.1016/0040-4020(77)80448-1 CASWeb of Science®Google Scholar 210 W. Oppolzer, V. Snieckus, Angew. Chem. 90 (1978) 506; 10.1002/ange.19780900705 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 17 (1978) 476. 10.1002/anie.197804761 Web of Science®Google Scholar 211 W. A. McEwen, M. A. Hernandez, C. F. Ling, E. Marmugi, R. M. Pradonaggio, C. M. Zepp, III, J. J. Lubinkowski, J. Org. Chem. 46 (1981) 1656. 10.1021/jo00321a027 CASWeb of Science®Google Scholar 212 J. P. Kennedy, E. Marechal, J. Polym. Sci. Macromol. Rev. 16 (1981) 123. 10.1002/pol.1981.230160103 CASWeb of Science®Google Scholar 213 S. Iwatsuki, Y. Yamashita, Prog. Polym. Sci. Jpn. 2 (1971) 31. Google Scholar 214 F. E. Mulvaney, R. J. Cramer, H. K. Hall, Jr., J. Polym. Sci. Polym. Chem. Ed. 21 (1983) 309. 10.1002/pol.1983.170210130 CASWeb of Science®Google Scholar 215 N. Wiberg, Angew. Chem. 80 (1968) 809; 10.1002/ange.19680802002 Google Scholar Angew. Chem. Int. Ed. Engl. 7 (1968) 766. 10.1002/anie.196807661 CASWeb of Science®Google Scholar 216 W. A. Pryor, W. H. Hendrickson, Jr., J. Am. Chem. Soc. 97 (1975) 1580, 1582. 10.1021/ja00839a054 CASWeb of Science®Google Scholar 217 B. Belleau, Y. K. Au-Young, Can. J. Chem. 47 (1969) 2117. 10.1139/v69-343 CASWeb of Science®Google Scholar 218 N. L. Zutty, C. W. Wilson, G. H. Potter, D. C. Priest, C. J. Whitworth, J. Polym. Sci. A 3 (1965) 2781. 10.1002/pol.1965.100030806 CASWeb of Science®Google Scholar 219 G. Sartori, R. D. Lundberg, J. Polym. Sci. Polym. Lett. Ed. 10 (1972) 583. 10.1002/pol.1972.110100802 CASWeb of Science®Google Scholar 220 S. Aoki, R. F. Tarvin, J. K. Stille, Macromolecules 3 (1970) 472. 10.1021/ma60016a020 CASWeb of Science®Google Scholar 221 C. Chatgilialoglu, K. U. Ingold, J. Am. Chem. Soc. 103 (1981) 4833. 10.1021/ja00406a027 CASWeb of Science®Google Scholar Citing Literature Volume95, Issue6Juni 1983Pages 448-464 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
Referência(s)