Amines as Dehalogenating Agents, IIΙ The Fate of Ν,Ν-Dimethylaniline in the Reductive Dehalogenation of 3-Bromocamphor

Abstract

A product analysis was made for the reaction between some aromatic amines and 3-bromocamphor (2), which was invariably transformed into camphor (3) and eventually aryliminocamphor. The tertiary N,N-dimethylanilines were oxidized through a complex sequence of couplings and rearrangements to a number of diamines of the diphenylmethane type. Aniline (4) was also successful in the reductive debromination of 2 to 8 and camphor anil (7), but gave only tarry amino compounds. The reaction, carried out at 200 °C, appeared most probably to be triggered by the radicalic dissociation of the C-Br bond. Bromine ended up as bromide ion in a quantitative fashion.