ADDITION AND DISPLACEMENT REACTIONS WITH UNSATURATED HYDROCARBONS.

Abstract

The cuprous-bromide-catalyzed reaction of t-butyl perbenzoate and bicyclo-(3.2.1)-octene-2 (I) results in the formation of exo(axial) -bicyclo-(3.2.1)-oct-3-en-2-yl benzoate (IIIa) which contains < 1% of the endo isomer. Optically active I gives racemic IIIa which means that the allylic carbon atoms (C2 and C4) are completely randomized. These results are consistent with the Kochi mechanism; i.e., abstraction of an allylic hydrogen atom to give the symmetrical bicyclo(3.2.1)oct-3en2-yl radical (II) which is stereoselectively converted to racemic exo benzoate (IIIa). (Progress is also reported of studies concerning the solvolysis of alpha-p-anisylethyl p-nitrobenzoate (ROCOC6H4NO2) under various conditions.) (Author)

Document Details

Document Type
Technical Report
Publication Date
Apr 14, 1964
Accession Number
AD0600223

Entities

People

  • Harlan L. Goering

Organizations

  • University of Wisconsin–Madison

Tags

DTIC Thesaurus Topics

  • Benzoates
  • Chemical Compounds
  • Chemical Reactions
  • Displacement
  • Displacement Reactions
  • Hydrocarbons
  • Hydrogen
  • Organic Compounds
  • Solvolysis
  • Unsaturated Hydrocarbons

Fields of Study

  • Chemistry

Readers

  • Geochemistry
  • Organic Chemistry