The reaction of oximes with tributylphosphine–phenyldisulfide: mechanistic insight and new synthetic possibilities

Reduction of oximes to imines with tributylphosphine–phenyldisulfide reagent proceeds via formation of phenylthioimino intermediates which are subsequently reduced to imines with tributylphosphine in the presence of a proton source. The latter reaction provides the first practical method for convers...

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Bibliographic Details
Published in:Tetrahedron 2002-01, Vol.58 (2), p.215-219
Main Authors: Lukin, K.A., Narayanan, B.A.
Format: Article
Language:English
Subjects:
imines
oximes
reduction
thioimines
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Summary:Reduction of oximes to imines with tributylphosphine–phenyldisulfide reagent proceeds via formation of phenylthioimino intermediates which are subsequently reduced to imines with tributylphosphine in the presence of a proton source. The latter reaction provides the first practical method for conversion of phenylthioimines into ketones. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)01154-1