Substituent effects on cyclobutyl and cyclopropylcarbinyl cations

KB Wiberg, D Shobe, GL Nelson

Index: Wiberg, Kenneth B.; Shobe, David; Nelson, Gordon L. Journal of the American Chemical Society, 1993 , vol. 115, # 23 p. 10645 - 10652

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Citation Number: 46

Abstract

Abstract: The acetolyses of 3-substituted cyclobutyl tosylates (X= Ar, C1, and OEt) were examined giving rate constants and product distributions. With the alkyl-and aryl-substituted compounds, the rate-determining step leads to the formation of a bridged cyclobutyl cation which then rearranges to a cyclopropylcarbinyl/homoallyl ion. The value of p for the solvolysis of the 3-aryl derivatives was-1.5, suggesting some charge transfer to the 3- ...

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