Reaction of stabilised phosphorus ylides with nitrogen dioxide

Article abstract of DOI:10.1002/(SICI)1099-0690(199901)1999:1<251::AID-EJOC251>3.0.CO;2-M

The reaction of the stabilised ylides 14-23 with an excess of NO₂ in CH₂Cl₂ 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 Ph₃PO · HNO₃ (24) which has been fully characterised for the first time. Under the same conditions, the ylide 18 gives 2,4-dinitrobenzonitrile (26), Ph₃PO, and benzoic acid. The other ylides examined all give 24 together with a variety of other products.