Title

Limitations on the Persistence of Iminoxyls: Isolation of tert-Butyl 1,1-Diethylpropyl Ketiminoxyl and Related Radicals

Document Type

Article

Publication Date

1-1-1997

Abstract

A series of iminoxyl radicals of the general formula R(C=NO•)R1, with R and R1 usually tertiary, was synthesized in a search for radicals of increased persistence. Three new radicals were isolated as blue liquids: Et3C(C=NO•)Bu-t (1), t-C5H11(C=NO•)Bu-t (2), and (t-C5H11)2C=NO• (3). Oxidation of oximes Et3C(C=NOH)Ph (4H), PhCH2CMe2(C=NOH)Bu-t (5H), PhCMe2(C=NOH)Bu-t (6H), and Me2CH(C=NOH)C5H11-t (7H), among others, did not lead to isolable iminoxyls. A new, convenient synthesis of symmetrical tertiary imines from tert-RCl, tert-RCN, and Na is described. Radical t-Bu2C=NO• (8) and cyclohexene readily gave the allylic substitution product, 2,2,4,4-tetramethyl- 3-hexanone O-(2′-cyclohexen-1′-yl)oxime.

Publication Title

Journal of Organic Chemistry

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