OXIDATION OF ARYLOXYAMINOALCOHOLS WITH ACTIVATED DIMETHYLSULFOXIDE - A NOVEL C-N OXIDATION FACILITATED BY NEIGHBORING GROUP EFFECT

Oxidation of aryloxy-.beta.-aminopropanois (1) with "activated" dimethylsulfoxide (DMSO) was found to provide a convenient "one-pot" method to synthesize aryloxy-.beta.-aminoketooximes (3), without isolation of the unstable ketones 2. Assignment of Z and E stereoisomers of oximes...

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Bibliographic Details
Published inTetrahedron Vol. 45; no. 13; pp. 4091 - 4102
Main Authors SIMAY, A, PROKAI, L, BODOR, N
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1989
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Oxidation of aryloxy-.beta.-aminopropanois (1) with "activated" dimethylsulfoxide (DMSO) was found to provide a convenient "one-pot" method to synthesize aryloxy-.beta.-aminoketooximes (3), without isolation of the unstable ketones 2. Assignment of Z and E stereoisomers of oximes 3 was based on 1H- and 13C-NMR studies. Spontaneous isomerization of 3 was also observed and discussed. Dioxime derivatives 6 and 7 were first isolated as by-products in the oxidation of compounds 1 and an improved synthetic method for 6 was developed. The novel C-N oxidation step involved in the formation of 6 from 1 was rationalized on the basis of neighboring group effect.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)81305-3