Rules for ring closure. Stereoelectronic control in the endocyclic alkylation of ketone enolates

JE Baldwin, LI Kruse

Index: Baldwin,J.E.; Kruse,L.I. Journal of the Chemical Society, Chemical Communications, 1977 , p. 233 - 235

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Citation Number: 52

Abstract

Summary Endocyclic alkylation of ketone enolates is shown to depend critically upon the size of the so formed ring and six- but not five-membered cyclic ketones can be synthesized in this way; a rationale for this difference is presented. ... KETONIC substances of the general type (1) can be de- protonated to the isomeric enolates (2) or (3) which, in principle, may be intramolecularly alkylated (when Y is a leaving group) to the ring structures (4) or (5). Since these ...