Intramolecular hydride shift in some noncyclic isopropyl ketols

EW Warnhoff, MYH Wong…

Index: Warnhoff, E. W.; Wong, Margaret Y. H.; Raman, P. Sundara Canadian Journal of Chemistry, 1981 , vol. 59, p. 688 - 696

Full Text: HTML

Citation Number: 8

Abstract

The acyclic ketols have been synthesized by a Reformatsky sequence. Each ketol undergoes intramolecular hydride transfer when refluxed in KOH-H2O-t-BuOH solution. When the procedure was applied to the synthesis of 34, hydride transfer occurred during the Reformatsky reaction to yield 33 instead. With longer reaction times, 33 underwent self- acylation and β-dicarbonyl cleavage to 37. Treatment of 33 with aqueous base gave a ...