THE PHOTOCHEMISTRY OF IODO, METHYL AND THIOMETHYL SUBSTITUTED ARYL AZIDES IN TOLUENE SOLUTION AND FROZEN POLYCRYSTALS
- 1 September 1991
- journal article
- Published by Wiley in Photochemistry and Photobiology
- Vol. 54 (3) , 329-333
- https://doi.org/10.1111/j.1751-1097.1991.tb02024.x
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.Keywords
This publication has 14 references indexed in Scilit:
- Photoaffinity heterobifunctional crosslinking reagents based on N-(azidobenzoyl)tyrosinesBioconjugate Chemistry, 1990
- Aryl azides as photolabels. Retention of iodine during photochemical ring expansion of an iodinated tyrosine derivativeTetrahedron Letters, 1990
- Photochemistry of fluorinated aryl azides in toluene solution and in frozen polycrystalsThe Journal of Organic Chemistry, 1989
- 1,2-Didehydroazepines from the photolysis of substituted aryl azides: analysis of their chemical and physical properties by time-resolved spectroscopic methodsJournal of the American Chemical Society, 1988
- EPR spectroscopy of triplet aryl nitrenes covalently bound to .alpha.-chymotrypsin. Application of low-temperature methods to photoaffinity labelingJournal of the American Chemical Society, 1988
- A formal CH insertion reaction of an aryl nitrene into an alkyl CH bond. Implications for photoaffinity labelling.Tetrahedron Letters, 1986
- High yields of formal CH insertion products in the reactions of polyfluorinated aromatic nitrenesJournal of the American Chemical Society, 1986
- Photochemistry of phenyl azide: the role of singlet and triplet phenylnitrene as transient intermediatesJournal of the American Chemical Society, 1986
- Photochemistry of phenyl azide: chemical properties of the transient intermediatesJournal of the American Chemical Society, 1984
- ARYL AZIDES AS PHOTOAFFINITY LABELS. A PHOTOCHEMICAL STUDY OF SOME 4-SUBSTITUTED ARYL AZIDESPhotochemistry and Photobiology, 1982