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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.