Reactions of Trimethylsilyl Cyanide and N-(Trimethylsilyl)diphenylmethyleneamine with Nitrones and Thermal Decompositions of Their Adducts

Article abstract of DOI:10.1246/bcsj.53.485

Trimethylsilyl cyanide (1) and N-(trimethylsilyl)diphenylmethyleneamine (2) reacted with α-aryl-N-phenylnitrones to afford the corresponding 1:1 adducts 4 and 5 respectively.Thermal decomposition of 4 in refluxing xylene gave azoxybenzene, stereoisomers of 2,3-diarylsuccinonitriles, α-aminonitriles and/or benzanilides, whose yields depended on the nature of substituents on phenyl group of 4.On heating in benzene 5 afforded a mixture of azoxybenzene and meso-N,N'-bis(diphenylmethylene)-1,2-diarylethylenediamines.On the other hand, reactions of 1 and 2 with N-(diphenylmethylene)aniline N-oxide or N-(9-fluorenylidene)aniline N-oxide did not give the corresponding 1:1 adducts, but instead compounds arising from thermal decomposition of initial 1:1 adducts were directly obtained.The reaction of 1 with N-(p-diethylaminophenyl)-α-phenylnitrone leading to the corresponding α-imino nitrile is also described.