SMALL-RING COMPOUNDS. XLI. THE FORMOLYSIS OF ALLYLCARBINYL TOSYLATE,

Abstract

Allylcarbinyl tosylate was found to solvolyze in 98% formic acid 3.7 times faster than n-butyl tosylate. Changes in the rate ratio with nucle ophilicity of the solvent suggests different mechanisms for these solvolyses. The formolysis products of allylcarbinyl tosylate were found to be virtually identical with those from cyclobutyl tosylate. Deuterium labeling experiments indi cated complete scrambling ofe3e methylene groups in the ring-closed products. The results are interpreted in terms of formation of bicyclobu tonium ion intermediates. (Author)

Document Details

Document Type
Technical Report
Publication Date
Dec 01, 1963
Accession Number
AD0426962

Entities

People

  • John D. Roberts
  • Kenneth L. Servis

Organizations

  • California Institute of Technology

Tags

DTIC Thesaurus Topics

  • Acyclic Hydrocarbons
  • Alkenes
  • Carboxylic Acids
  • Chemical Compounds
  • Deuterium
  • Elements
  • Formic Acid
  • Group 1 Elements
  • Methylenes
  • Organic Compounds

Fields of Study

  • Chemistry

Readers

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