The Journal of Organic Chemistry

Molecular rearrangements. 13. Kinetics and mechanism of rearrangements of some ring-substituted. alpha.-chlorostyrene oxides and trans-. beta.-chlorostyrene …

RN McDonald, RC Cousins

Index: McDonald, Richard N.; Cousins, Raymond C. Journal of Organic Chemistry, 1980 , vol. 45, # 15 p. 2976 - 2984

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Citation Number: 32

Abstract

The synthesis of certain phenyl-substituted derivatives of the isomeric trans-P-chlorostyrene oxides (6) and a-chlorostyrene oxides (7) are reported. The kinetics of rearrangement of 6 (X= p-CH3, H, p-Br, m-C1, p-NO,) to phenylchloroacetaldehydes (12) in CC14 buffered by Na2HP04 and 7 (X= p-CH3, H, p-NO,) to w-chloroacetophenones in CC14 were determined by following the rates of disappearance of the a-chloro epoxide and formation of the a- ...