THE PHOTOCHEMISTRY OF IODO, METHYL AND THIOMETHYL SUBSTITUTED ARYL AZIDES IN TOLUENE SOLUTION AND FROZEN POLYCRYSTALS

Elisa Leyva, David H.S. Chang, Matthew S. Platz, David S. Watt, Peter J. Crocker, Kenji Kawada

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The photolysis of para‐methyl and para‐thiomethylphenylazide at 77 K produces the corresponding triplet nitrenes which can be detected by electron paramagnetic resonance (EPR) spectroscopy. Photolysis of these azides in frozen toluene at 77 K leads to insertion of the nitrene into a benzylic C‐H bond of the matrix in modest yields. Photolysis of iodinated aryl azides under these conditions does not produce triplet nitrenes that can be detected by EPR spectroscopy. In contrast to the para‐methyl and para‐thiomethyl substituted phenyl nitrenes, photo‐induced cgupling of iodo‐substituted phenyl nitrenes to toluene proceeds in very poor yield.

Original languageEnglish
Pages (from-to)329-333
Number of pages5
JournalPhotochemistry and Photobiology
Volume54
Issue number3
DOIs
StatePublished - Sep 1991

ASJC Scopus subject areas

  • Radiation
  • Biochemistry
  • Physical and Theoretical Chemistry

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