4b ;3',diisothiazole-1-carbonitrile (27). A solution of tetraethylammonium cyanide (1.7 g, 0.01 mol) in acetonitrile (50 mL) was added over a 15-min period to a solution of 26 (3.3 g, 0.01 mol) in acetonitrile (100 mL) at 15 °C, and crude 27 (2.21 g, 98%) was isolated by filtration. Compound 27 was washed with acetonitrile and ether. Recrystallization from n-butyl chloride (or acetone) gave analytically pure 28:

No abstract

No abstract

distilled in a Kugelrohr apparatus at 140-145 °C (0.02 torr) to afford GLC-pure product (6.85 g) as a yellow liquid: 38% yield as 7;

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.