90466-00-5Relevant articles and documents
Synthesis and Reactions of Phenolic Alkylbenzylnitrosamines
Bowman, Peter J.,Brown, Ben R.,Chapman, M. Andrew,Doyle, Paul M.
, p. 701 - 770 (2007/10/02)
N-Alkyl-p-hydroxybenzylnitrosamines have been synthesised from p-benzoyloxybenzaldehydes via imines and amines which were nitrosated before removal of the protecting group with n-propylamine.N-Alkyl-o-hydroxybenzylnitrosamines were similarly obtained from o-methoxymethoxybenzaldehydes, the final deprotection being achieved with dilute acid.The nitrosamines decompose in hot aqueous alkali by two mechanisms, one through a quinone methide to yield a benzyl alcohol and the other by an elimination eventually yielding a benzaldehyde.The decomposition of the nitrosamines in the presence of 2-naphthol in alkaline solution results in alkylation of the naphthol and production of compounds from the reaction of 2-naphthol with the intermediate quinone methides.The N-sec-butylnitrosamines alkylate 2-naphthol on carbon but the N-methylnitrosamines alkylate on oxygen and during the methylation 94percent of deuterium exchange with methyl hydrogen occurs in deuterium oxide and there is 6percent intact transfer of the methyl group from the N-methylnitrosamine to the 2-naphthol.
