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THE PHOTOCHEMISTRY OF 3‐NITROBENZOYL AND 4‐NITROBENZOYL AZIDES: POSSIBLE REAGENTS FOR PHOTOAFFINITY LABELING
Author(s) -
Woelfle Ingrid,
Sauerwein Björn,
Autrey Tom,
Schuster Gary B.
Publication year - 1988
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1988.tb08837.x
Subject(s) - nitrene , chemistry , nucleophile , photoaffinity labeling , reagent , photochemistry , singlet state , combinatorial chemistry , organic chemistry , catalysis , binding site , excited state , biochemistry , physics , nuclear physics
— The photochemistry of 3‐ and 4‐nitrobenzoyl azides was studied to examine their suitability for use in photolabeling procedures. These aroyl azides absorb light in the near UV‐spectral region. Their irradiation leads both to photo‐Curtius rearrangement with formation of the analogous isocyan‐ates and to generation of nitrenes by loss of nitrogen. The chemical and spectroscopic properties of the aroyl nitrenes indicate that they are singlets in their ground states. These singlet nitrenes insert rapidly into unactivated, aliphatic carbon‐hydrogen bonds, trap nucleophiles, and add to olefins to form aziridines with retention of stereochemistry. Photolabeling agents based on these azides may offer some advantages over conventional agents for the labeling of lipophilic sites.