Silver (I) catalyzed rearrangements of strained. sigma. bonds. 38. Regiospecificity of cyclopropylidene carbon-hydrogen insertion reactions within [mn 1] propellane …

LA Paquette, E Chamot, AR Browne

文献索引：Paquette,L.A.; Chamot,E.; Brown,A.R. Journal of the American Chemical Society, 1980 , vol. 102, p. 637

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被引用次数: 17

摘要

Abstract: Dibromocyclopropanes, which form an integral part of [mn I jpropellanes, undergo smooth conversion to the carbenoid (quite likely an epimeric a-haloalkyllithium mixture) when treated with methyllithium. The ensuing cyclizations to bicyclo [1. I. O] butane-type products are regiospecific, the relative reactivity order of the C,-H bonds being cyclopentyl> norcaranyl-I-tetralyl> cyclohexyl> cyclohexenyl. A mechanism involving loss of lithium ...