Ionic reactions in the spirane series. I. Effect of adjacent ring size on the acetolysis of neopentyl-type tosylates of the spirane series

A. Paul Krapcho, Merrill Benson

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5 Citations (Scopus)

Abstract

The acetolysis of several spirane tosylates (VI, n = 2, 3 and 4) of the neopentyl-type has been studied. The acetolysis rate was found to he dependent on adjacent ring size and the products of the acetolysis were predominantly olefins resulting from rearrangement. The results are discussed in terms of the effect of ring strain on anchimeric assistance in rearrangements of the Wagner-Meerwein type.

Original languageEnglish (US)
Pages (from-to)1036-1040
Number of pages5
JournalJournal of the American Chemical Society
Volume84
Issue number6
StatePublished - 1962
Externally publishedYes

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Olefins

ASJC Scopus subject areas

  • Chemistry(all)

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title = "Ionic reactions in the spirane series. I. Effect of adjacent ring size on the acetolysis of neopentyl-type tosylates of the spirane series",
abstract = "The acetolysis of several spirane tosylates (VI, n = 2, 3 and 4) of the neopentyl-type has been studied. The acetolysis rate was found to he dependent on adjacent ring size and the products of the acetolysis were predominantly olefins resulting from rearrangement. The results are discussed in terms of the effect of ring strain on anchimeric assistance in rearrangements of the Wagner-Meerwein type.",
author = "{Paul Krapcho}, A. and Merrill Benson",
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AU - Paul Krapcho, A.

AU - Benson, Merrill

PY - 1962

Y1 - 1962

N2 - The acetolysis of several spirane tosylates (VI, n = 2, 3 and 4) of the neopentyl-type has been studied. The acetolysis rate was found to he dependent on adjacent ring size and the products of the acetolysis were predominantly olefins resulting from rearrangement. The results are discussed in terms of the effect of ring strain on anchimeric assistance in rearrangements of the Wagner-Meerwein type.

AB - The acetolysis of several spirane tosylates (VI, n = 2, 3 and 4) of the neopentyl-type has been studied. The acetolysis rate was found to he dependent on adjacent ring size and the products of the acetolysis were predominantly olefins resulting from rearrangement. The results are discussed in terms of the effect of ring strain on anchimeric assistance in rearrangements of the Wagner-Meerwein type.

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JF - Journal of the American Chemical Society

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