Smiles‐Umlagerung eines Pyridylsulfoxids | Zendy

Braun Manfred | Zendy; Hild Wilhelm | Zendy

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Smiles‐Umlagerung eines Pyridylsulfoxids

Author(s) -

Braun Manfred,

Hild Wilhelm

Publication year - 1986

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19861190729

Subject(s) - chemistry , smiles rearrangement , sulfoxide , benzaldehyde , tetrahydrofuran , sulfenic acid , sulfinic acid , diastereomer , medicinal chemistry , sulfone , lithium (medication) , stereochemistry , organic chemistry , catalysis , medicine , cysteine , solvent , enzyme , endocrinology

Smiles Rearrangement of a Pyridyl Sulfoxide The diastereomeric alkoxides 2b/3b , generated in situ by addition of the lithiated sulfoxide 1b to benzaldehyde, afford the disulfide 4 in tetrahydrofuran/hexamethylphosphoric triamide at room temperature. Obviously, a Smiles rearrangement of the lithium salts 2b/3b leads — via the intermediate 7 – to the sulfenic acid 8 which disproportionates to give the product 4 and sulfinic acid.

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