Ring-Size Effects in the Neophyl Rearrangement. V. The Carbenoid Decomposition of 1-Phenylcycloalkanecarboxaldehyde Tosylhydrazones

JW Wilt, JM Kosturik, RC Orlowski

文献索引：Wilt,J.W. et al. Journal of Organic Chemistry, 1965 , vol. 30, p. 1052 - 1057

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被引用次数: 14

摘要

1-Phenylcycloalkylcarbenes (5) have been prepared in sttu by the decomposition of l- phenylcycloalkanecarboxaldehyde tosylhydrazones with sodium methoxide in N-methyl-2- pyrrolidone at 180'(the aprotic Bamford-Stevens reaction). These reactive intermediates (5) rearrange to mixtures of hydrocarbons iii good yield, with varying degrees of phenyl migration and alkyl migration (ring expansion). The percentage of phedyl migration (the ...