N-demethylation of N,N-dimethylanilines by photoexcited 3-nitrochlorobenzene

✍ Scribed by Dietrich Döpp; Jörg Heufer

• Book ID: 104220655
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 236 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87156-7

✦ Synopsis

The title reaction proceeds via initial electron transfer (rather than hydrogen atom transfer) from the amine to the photoexcited nitro compound, as demonstrated by methoxy substitution in the substrate and absence of CH3/CD3-discrimination.

In 1974, Takami Matsuura and Saito 4) A briefly reported the efficient demethylation of N,N-dimethylaniline (la) by photoexcited 3-chloronitrobenzene (2) in benzene solution.

H3KN.CH3

12 g! 4 =

The authors suggested an initial hydrogen abstraction from a N-methyl group of L effected by photoexcited 2 as the first step in a sequence of reactions ultimately leading to demethyla-4) tion