Rapid nitrosamine formation from a tertiary amine: The nitrosation of 2-(N,N-Dimethylaminomethyl)pyrrole

✍ Scribed by R.N. Loeppky; J.R. Outram; W. Tomasik; J.M. Faulconer

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 267 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88318-5

✦ Synopsis

2-(N,N-Dimethylaminomethyl)pyrrole reacts instantaneously with nitrous acid at 25" to produce diemthylnitrosamine, maleimidemonooxine, formaldehyde and other products. The data implicate new mechanisms of tertiary amine nitrosation. N-Alkyl tertiary amines react very slowly at 25" with nitrous acid but at higher temperatures they produce nitrosamines and an aldehyde or ketone in good yields. A mechanism for this reaction has been postulated' and is supported by various experiments' as well as recent rate data'. We report here that 2-(N,N-dimethylaminomethyl)pyrrole l_, a model for the malt 'NO 17 SCHEME :" N I; H also suggests that other similar tertiary amines could rapidly produce nitrosamines under mild conditions.

Research in this area continues in our laboratory.