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Reaction of Stabilised Phosphorus Ylides with Nitrogen Dioxide
Author(s) -
Aitken R. Alan,
Karodia Nazira
Publication year - 1999
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/(sici)1099-0690(199901)1999:1<251::aid-ejoc251>3.0.co;2-m
Subject(s) - ylide , chemistry , nitrogen dioxide , phosphorus , benzoic acid , nitrogen , organic chemistry , medicinal chemistry , inorganic chemistry
The reaction of the stabilised ylides 14–23 with an excess of NO 2 in CH 2 Cl 2 at room temperature gives different results depending on the structure of the starting ylide. The monacyl ylides 14–16 give the corresponding α‐oxo nitriles 4 together with Ph 3 PO · HNO 3 ( 24 ) which has been fully characterised for the first time. Under the same conditions, the ylide 18 gives 2,4‐dinitrobenzonitrile ( 26 ), Ph 3 PO, and benzoic acid. The other ylides examined all give 24 together with a variety of other products.