The Journal of Organic Chemistry

Bromomethyl ketones and enolates: alternative products from ester homologation reactions

CJ Kowalski, MS Haque

Index: Kowalski, Conrad J.; Haque, M. Serajul Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5140 - 5142

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Citation Number: 44

Abstract

&fl C CH2Br 2, 9 a (80%) b (80%) ketone precursors, since the competing pathway 2-3-6 predominates for such compounds even at low temperatures. One exception to this case proved to be the mixture of exo/endo esters 28a and 28b, which afforded only the bromomethyl ketones 29a and 29b (each in 80% yield). This result suggests the bridgehead methoxy group in 28 served to stabilize the tetrahedral intermediate 2, either through ...