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Nitrosyl halides addition reactions

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. [Pg.500]

TFE undergoes free radical addition reactions typical of other olefins. It readily adds Br, Cl, and I, halogen halides IBr and ICl, and nitrosyl halides such as NOCl and NOBr. Additional reactions of chloro-fluoromethanes and chloromethanes in the presence of catalysts like aluminum chloride have been reported [48]. A variety of other compounds such as alcohols, primary amines and ammonia can be reacted with TFE to prepare tetrafluoroethers (HCF CF OR), difluoroacetamide (HCF CONHR) and substituted triazines. Oxygen can be added to TFE to produce polymeric peroxide or TFE epoxide. In the absence of hydrogen, sodium salts of alcohols will react with TFE to yield trifluorovinylethers (ROCF = CF ), which can be homo- and copolymerized. [Pg.59]


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