Journal of the American Chemical Society

Small-Ring Compounds. XIII. The Mechanism of Racemization of Optically Active 2, 4-Dichloro-3-phenylcyclobutenone1

EF Jenny, JD Roberts

Index: Jenny; Roberts Journal of the American Chemical Society, 1956 , vol. 78, p. 2005,2009

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Citation Number: 32

Abstract

I Enolization of 1 does not occur readily. The compound gives no color with ferric chloride solution and shows no hydroxyl absorption in the infrared. 3 It dissolves in alkali, but acidification yields 2, 4-dichloro-3-phenyl-3-butenoic acid and complex prod~ cts.~ No reaction was noted in an attempt to convert I to 1-acetoxy-2, 4-dichloro-3- phenylcyclobutadiene with isopropenyl acetate in the presence of p-toluenesulfonic acid ...