Nitrosyl halides reactions with alkenes

Nitrosyl halides add to alkenes references are scattered through the litnnture back to 1875 (ref. 194 and references cited therein). The adducts vary enormously in their stability, but when their structures allow they, like nonhalogenated nitroso compounds, isomerize to oximes or dimnize. The orientation of the reaction is consistent with an electrophilic medumism, in which the reagent is polarized as NO Hat. Bicyclic substrates and reaction media of low polarity favor syn addition, suggesting a four-center transition state (Scheme 81). Aziridine synthesis via NOCl/alkene adducts is discussed in Section 3.5.2.1. 

A number of metal nitrosyl complexes react with activated alkyl halides to yield, ultimately, organic nitrogen-containing products. The most widely studied reagent is [Ru(NO)2(PPh3)2] (229), though other compounds such as [CoCl(NO)(CO)2] (230) and [Fe(NO)(CO)3] (231) have been used. These reactions have been discussed in depth elsewhere (6). Another reaction of some industrial importance is the catalytic reaction of NO gas with alkenes. Over Ag20 or PbO the product from propene is acrylonitrile. In a study of this type of reaction (232),... 

---