The Journal of Organic Chemistry

Dialkylation of ketone dianions

RB Bates, SR Taylor

Index: Bates, Robert B.; Taylor, Stuart R. Journal of Organic Chemistry, 1994 , vol. 59, # 1 p. 245 - 246

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Citation Number: 13

Abstract

a, &-Dianions 1 from ketones were first prepared by Hubbard and Harris' by the metalation of potassium enolates with n-butyllithium. They reacted these dianions with 1 equiv of an electrophile at-78" C to 0 OC and protonated the resulting monoenolates 2 to give monoalkylatsd ketones 3 (Scheme 1). They knew they had prepared dianions since monoenolates did not react readily with their electrophiles at these low temperatures. ...