C-Nitroso compounds. Part XXXII. Reaction of α-chloro nitroso compounds with alkyl substituted allenes. A route to cross-conjugated aliphatic ketonitrones

Reaction of α-chloro nitroso compounds with tetramethylallene gives rise to the formation of hitherto unknown crystalline cross-conjugated nitrone hydrochlorides 3, which can be converted into free nitrones 4 upon treatment with liquid ammonia. The reaction between 2-chloro-2-nitrosoadamantane and 3-phenyl-1,2-butadiene proceeds equally well, but with other α-chloro nitroso compounds and with other alkylallenes only complicated mixtures are obtained, which contain the corresponding nitrone hydrochlorides as judged from hydrolysis to ketone and oxime 6.