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

Research output: Contribution to journalArticle

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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 be 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
DOIs
StatePublished - Jan 1 1962

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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