Journal of Organic Chemistry p. 5157 - 5160 (1986)
Update date:2022-08-04
Topics:
Biehl, Edward R.
Razzuk, Aziz
Jovanovic, Misa V.
Khanapure, Subhash P.
4-Bromo-1,2-dimethylbenzene (4a) reacts with a variety of amines, mercaptans, and nitriles under aryne-forming conditions to yield predominantly 4-substituted 1,2-dimethylbenzenes and minor quantities of 3-substituted 1,2-dimethylbenzenes.The product distributions from these reactions are heavily in favor of the 4-substituted isomer since it is formed exclusively from the symmetric 4,5-dimethylbenzyne intermediate (6) and partly from the unsymmetric 3,4-dimethylbenzyne intermediate (5).
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