Abstract
Abstract Trimethylsilyl cyanide (1) and N-(trimethylsilyl)diphenylmethyleneamine (2) reacted with α-aryl-N-phenyl-nitrones 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-iminonitriles 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.
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