Photosensitized Rearrangements of Triarylmethyl Azides

Frederick D. Lewis, William H. Saunders

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

The loss of nitrogen and rearrangement to benzophenone phenylimine of triphenylmethyl azide can be effected by photolysis in the presence of a variety of triplet sensitizers. The sensitizers definitely produced a reaction range in triplet energy from 67.6 kcal/mole (fluorene) to 48.7 kcal/mole (pyrene), so the triplet energy of triphenylmethyl azide must be less than 48.7 kcal/mole. Migration aptitudes in the photolysis sensitized by triphenylene of diphenyl(p-X-phenyl)methyl azides (X = NO2, Cl, CH3, OCH3, N(CH3)2) were all close to unity, as previously observed3 in the direct photolysis. It is concluded that both the direct and sensitized photolyses involve a triplet azide and probably a discrete triplet nitrene as intermediates.

Original languageEnglish (US)
Pages (from-to)645-647
Number of pages3
JournalJournal of the American Chemical Society
Volume89
Issue number3
DOIs
StatePublished - Dec 1 1967

ASJC Scopus subject areas

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

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