The Journal of Organic Chemistry

Ring Size Effects in the Neophyl Rearrangement1, 2

JW WILT, BH PHILIP

Index: Wilt,J.W.; Philip,B.H. Journal of Organic Chemistry, 1960 , vol. 25, p. 891 - 899

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Citation Number: 11

Abstract

1-Phenylcyclopentylacetaldehyde (I) and 1-phenylcyclohexylacetaldehyde (11) have been prepared and characterized. The rearrangement percentages upon di-t-butyl peroxide- induced decarbonylation in the liquid phase under various conditions have been determined (Table V). The results indicate that the 1, 2-phenyl shift is markedly more facile in I1 than in I. arguments are presented that this ring size effect results from differences in ...