Intramolecular carbon-hydrogen insertions of alkylidenecarbenes. I. Selectivity

…, DH Giamalva, U Weerasooriya

Index: Gilbert, John C.; Giamalva, David H.; Weerasooriya, Upali Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5251 - 5256

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Citation Number: 75

Abstract

Base-promoted reaction between dialkyl ketones having y-hydrogens and dialkyl (diazomethy1) phosphonates leads to formation of cyclopentenes in modest to high yields. The relative reactivity of various types of carbon-hydrogen bonds for the process, which involves insertion by an alkylidenecarbene, has been assessed, and the result has been compared to those reported when the carbene is generated by a elimination and by 1, 2- ...