REACTIVE INTERMEDIATES FROM THE SOLVOLYSIS OF MUTAGENIC O-ALKYL N-ACETOXYBENZOHYDROXAMATES

Authors
BONIN AM GLOVER SA HAMMOND GP
Citation
Am. Bonin et al., REACTIVE INTERMEDIATES FROM THE SOLVOLYSIS OF MUTAGENIC O-ALKYL N-ACETOXYBENZOHYDROXAMATES, Perkin transactions. 2, (6), 1994, pp. 1173-1180
Citations number
21
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Perkin transactions. 2 → ACNP
ISSN journal
03009580
Issue
6
Year of publication
1994
Pages
1173 - 1180
Database
ISI
SICI code
0300-9580(1994):6<1173:RIFTSO>2.0.ZU;2-Q
Abstract
Mutagenic O-(para-substituted benzyl) N-acetoxybenzohydroxamates under go acid-catalysed solvolysis in aqueous acetonitrile but there is a ch ange in mechanism from A(A1)1 to E1 on going from para electron-withdr awing substituents to para +M electron-donating groups. The former per mit the formation of a discrete nitrenium ion intermediate whereas the latter promote a concerted elimination of a resonance stabilized benz yl carbocation.