Journal of Organic Chemistry p. 5612 - 5615 (1985)
Update date:2022-08-05
Topics:
Bergmark, William R.
Barnes, Curtis
Clark, Jeffrey
Paparian, Seth
Marynowski, Susan
Irradiation of a methanol solution of 2,5-dimethyl-α-chloropropiophenone (1a) produces 2,6-dimethyl-1-indanone (2a), 2-(methoxymethyl)-5-methylpropiophenone (3a), 2,5-dimethylpropiophenone (4a), and methyl 2-(2,5-dimethylphenyl)propionate (5a).It is proposed that the first two products arise from hydrogen abstraction followed by chlorine loss, the latter two from initial loss of chlorine.Making the chlorine-bearing carbon primary suppresses the formation of the latter two products, while maintaining the carbonyl nearly planar with the ring suppresses all product formation.Other examples are presented.
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(1983)