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15 N‐CIDNP during Photonitration of Phenol with Tetranitromethane and Reactions with Nitric and Nitrous Acid
Author(s) -
Lehnig Manfred,
Schürmann Klaus
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199805)1998:5<913::aid-ejoc913>3.0.co;2-r
Subject(s) - chemistry , tetranitromethane , nitrous acid , cidnp , radical , nitration , nitric acid , phenol , hydroquinone , photochemistry , organic chemistry , medicinal chemistry
During the irradiation of phenol ( 1 ) with 15 N‐enriched tetranitromethane in acetonitrile, and during the reaction of 1 with 15 N‐enriched nitric acid and nitrous acid, emission due to the nitration products o ‐ and p ‐nitrophenol ( 2a , 2b ) is observed in the 15 N‐NMR spectra. The CIDNP effects are built up by radical pairs formed by the encounters of the radicals NO 2 · and 1 +· or PhO · . During the reaction of 1 with nitrous acid, 2b is formed, in part due to a non‐radical reaction, via oxidation of p ‐nitrosophenol ( 3 ).