51468-52-1Relevant articles and documents
Reactivity of 3-Hydroxyimino-1,7,7-trimethyl-N-nitrobicycloheptan-2-imine (3-Hydroxyiminocamphornitrimine).
Ranise, Angelo,Bondavalli, Francesco,Schenone, Pietro
, p. 835 - 851 (2007/10/02)
3-Hydroxyiminocamphornitrimine (1) reacted exclusively at the oxime group with diazomethane and alkyl halides to give O-methyl ether (2) and other ethers, and with acetyl and benzoyl chloride to give the corresponding O-esters (8) and (9).As expected, (1) and (2) reacted exclusively at the nitrimino group with ammonia, aliphatic amines and carbonyl group reagents such as phenylhydrazine to afford the corresponding imines in high yields.Some reactions involving both nitrimino and hydroxyimino group of (1) were reductive deoximations, such as the reaction in certain conditions with hydroxylamine, semicarbazide, thiosemicarbazide and phenylhydrazine, whereby beside the expected carbonyl derivatives of 3-hydroxyiminocamphor the corresponding derivatives of camphor were also formed.Reduction of (1) with complex hydrides gave always a mixture of 3-hydroxyimino-1,7,7-trimethyl-N-nitrobicycloheptan-2-amine and bornylnitramine.Passerini reaction carried out on (9) with excess KCN afforded 3,3-dimethyl-2-methylenebicycloheptane-1-carboxamide in 95percent yield.
