A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

SZ Janicki, JM Fairgrieve, PA Petillo

Index: Janicki, Slawomir Z.; Fairgrieve, Jennifer M.; Petillo, Peter A. Journal of Organic Chemistry, 1998 , vol. 63, # 11 p. 3694 - 3700

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Citation Number: 14

Abstract

The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a-f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57-93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58-99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87-99% to produce enol ethers 31. ...