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O/NMe 2 exchange in the reaction of 4‐benzylidene‐5‐oxazolones with phosphorous tris(dimethylamide)
Author(s) -
Bansal Raj K.,
Karaghiosoff Konstantin,
Schmidpeter Alfred
Publication year - 1988
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.19881211128
Subject(s) - chemistry , pyrazolones , tris , adduct , medicinal chemistry , phosphorus , organic chemistry , stereochemistry , biochemistry
4‐Benzylidene‐5‐oxazolones 5 do not react with P(OMe) 3 ; with P(NMe 2 ) 3 they give rise to 4‐α‐[bis(dimethylamino)phosphoryl]benzyl‐5‐dimethylaminooxazoles 6 . This behavior differs from that of the corresponding pyrazolones and isoxazolones and is attributed to a decreased stability of the dipolar adduct resulting from a β attack of phosphorus.