Substituent effects on the regioselectivity of intramolecular carbene carbon-hydrogen insertion. Cyclizations of 1-and 5-substituted 2-adamantylidenes

S Hirsl-Starcevic, Z Majerski

Index: Hirsl-Starcevic, Sanja; Majerski, Zdenko Journal of Organic Chemistry, 1982 , vol. 47, # 13 p. 2520 - 2525

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Citation Number: 10

Abstract

Carbenes, 1-methyl-, 1-chloro-, &methyl-, and 5-chloro-2-adamantylidene, were generated by pyrolysis of dry tosylhydrazone alkali salts. Each of these carbenes yielded both possible products of the intramolecular CH insertion, the corresponding 1-and 3-substituted 2, 4- didehydroadamantanes or 1-and 7-substituted 2, 4-didehydroadamantanes. The product distribution varies considerably depending on the substituent and its position relative to ...