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Solvolysis of 7,7‐Bis(alkylthio)norcaranes. A New Method of Homologation

1972; Wiley; Volume: 11; Issue: 1 Linguagem: Inglês

10.1002/anie.197200491

1521-3773

Dieter Seebàch, Manfred Braun,

Inorganic and Organometallic Chemistry

Angewandte Chemie International Edition in EnglishVolume 11, Issue 1 p. 49-50 Communication Solvolysis of 7,7-Bis(alkylthio)norcaranes. A New Method of Homologation Prof. Dr. Dieter Seebach, Prof. Dr. Dieter Seebach Institut für Organische Chemie der Universität KarlsruheSearch for more papers by this authorDipl.-Chem. Manfred Braun, Corresponding Author Dipl.-Chem. Manfred Braun Institut für Organische Chemie der Universität KarlsruheInstitut für Organische Chemie der Universität KarlsruheSearch for more papers by this author Prof. Dr. Dieter Seebach, Prof. Dr. Dieter Seebach Institut für Organische Chemie der Universität KarlsruheSearch for more papers by this authorDipl.-Chem. Manfred Braun, Corresponding Author Dipl.-Chem. Manfred Braun Institut für Organische Chemie der Universität KarlsruheInstitut für Organische Chemie der Universität KarlsruheSearch for more papers by this author First published: January 1972 https://doi.org/10.1002/anie.197200491Citations: 16AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation 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 No abstract is available for this article. References 1 D. Seebach, Synthesis 1969, 17, and literature cited therein. 2 Compare also J. B. Jones and R. Grayshan, Chem. Commun. 1970, 141, 741. 3 J. P. O'Brien, A. I. Rachlin, and S. Teitel, J. med. Chem. 12, 1112 (1969); C. Feugeas and J. P. Galy, C.R. Acad. Sci. Paris C 270, 2157 (1970). 4 Analogous ring openings of dihalocarbene adducts to give halogen-free products are difficult: see. C. D. Gutsche and D. Redmore: Carbocyclic Ring Expansion Reactions. Academic Press, New York 1968. 5 Norcarane gives acetoxy-(2-hydroxy- or acetoxy-(2-acetoxy-cyclohexylmethyl)mercury(II) under these conditions: R. Y. Levina, B. N. Kostin, and T. K. Ustynyuk, Zh. Obshch. Khim. 30, 359 (1960); Chem. Abstr. 54, 54457 (1960); cf. A. De Boer and C. H. De Puy, J. Amer. Chem. Soc. 92, 4008 (1970). 6 (4) is probably formed from (5) through a carbonium ion [ F. R. Jensen and R. J. Oulette, J. Amer. Chem. Soc. 83, 4477, 4478 (1961); J. Amer. Chem. Soc. 85, 363, 367 (1963)]. 7 U. Schöllkopf, Angew. Chem. 80, 603 (1968); Angew. Chem. internat. Edit. 7, 588 (1968); U. Schöllkopf et al. Tetrahedron Lett. 1970, 5077; J. A. Landgrebe and L. W. Becker, J. Amer. Chem. Soc. 90, 395 (1968), and literature cited therein. Citing Literature Volume11, Issue1January 1972Pages 49-50 ReferencesRelatedInformation