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Spectral and kinetic measurements on a series of persistent iminoxyl radicals

✍ Scribed by Brian M. Eisenhauer; Minghui Wang; Richard E. Brown; Henryk Labaziewicz; Maria Ngo; Karl W. Kettinger; G. David Mendenhall

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 163 KB
Volume: 10
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199710)10:10<737::aid-poc944>3.0.co;2-n

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✦ Synopsis

A series of new iminoxyl radicals, Et 3 C(C=NO • )Bu-tert (1), tert-C 5 H 11 (C=NO • ) Bu-tert (2), (tert-C 5 H 11 ) 2 C=NO • (3), Et 3 C(C=NO • )Ph (4), PhCH 2 CMe 2 (C=NO • )Bu-tert (5), PhCMe 2 (C=NO • )Bu-tert (6) and Me 2 CH(C = NO • )C 5 H 11 -tert (7), was characterized by EPR and in some cases visible spectra and decay kinetics in solution. Isolation of 1H and 3-tertbutyl-4,4-diethyl-5-methyl-4,5-dihydro-5-isoxazolol (9) among the decomposition products of 1 was consistent with a previously unrecognized mode of iminoxyl reaction in which the initial step is an internal ␤-H abstraction. Molecular orbital calculations on H 2 C=NO • indicate a C-N-O angle of about 140° and a 10 kcal mol Ϫ 1 barrier to inversion. Rate constants for the reaction of tert-Bu 2 C=NO • (8) with a series of olefins were measured.

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