Singlet-Oxygenation of a Conjugated Diallene: Attempt to Prepare a Stable Divinyl Peroxide.

Abstract

A conjugated diallene, 2-3-divinylidenebicyclo(2.2.1)heptane, was prepared and isolated. Photosensitized oxygenation of this allene leads to two isolated oxygenated products in 50% yield. Detection of these products is interpreted to implicate an unstable cyclic divinyl peroxide intermediate. Attempts to detect this intermediate by low temperature nmr spectroscopy and by chemiluminescence were unsuccessful. The instability of this compound is attributed to the destabilizing lone pair interaction of the peroxide oxygen atoms. (Author)

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Document Details

Document Type
Technical Report
Publication Date
Aug 20, 1982
Accession Number
ADA118772

Entities

People

  • Gary Schuster
  • Robert C. Mebane

Organizations

  • University of Illinois Urbana–Champaign

Tags

Communities of Interest

  • Air Platforms
  • Ground and Sea Platforms

DTIC Thesaurus Topics

  • Chemical Reactions
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Inorganic Carbon Compounds
  • Liquid Chromatography
  • Magnetic Resonance
  • Materials
  • Materials Science
  • Military Research
  • New York
  • Organic Chemistry
  • Oxygen
  • Resonance
  • Spectra
  • Spectroscopy

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry
  • Polymer Science and Technology