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Phospha‐Michael‐Type Reactions between 1,2‐Diaza‐1,3‐dienes and Bidentate Nucleophiles: Formation of New Mono‐ and Diylides and their Elaboration to Heterocycles
Author(s) -
Boga Carla,
Zanicola,
Attanasi Orazio A.,
Baccolini Graziano,
De Crescentini Lucia,
Forlani Luciano,
Mantellini Fabio,
Nicolini Simona,
Micheletti Gabriele,
Tozzi Silvia
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001453
Subject(s) - chemistry , michael reaction , moiety , nucleophile , denticity , intramolecular force , methylene , reagent , medicinal chemistry , ylide , stereochemistry , organic chemistry , crystal structure , catalysis
Phospha‐Michael additions of a series of methylene‐bridged phosphorus bidentate nucleophiles to 1,2‐diaza‐1,3‐dienes gave monoadducts and bisadducts in high yields under mild conditions. In particular, a series of new ylides and symmetrical diylides have been obtained from bis(diphenyl)phosphanes. The use of diphenylphosphanylamino derivatives gave, through phospha‐Michael addition, ylide intermediates that underwent spontaneous intramolecular attack by the amino group belonging to the Michael donor reagent moiety, thus giving access to new heterocycles.