The synthesis of 1‐arylisochromans and their use in the preparation of ortho‐substituted diphenylmethane derivatives

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Abstract
Several 1‐arylisochromans were prepared from 1‐bromoisochroman and 1‐bromo‐4,4‐dimethylisochroman by reaction with arylmagnesium bromides. Bromination and heating yielded, presumably via bromo‐1‐arylisochromans, o‐(bromoalkyl)benzophenones. Treatment with lithium aluminium hydride converted the ketones into the corresponding carbinols, the side‐chain being simultaneously debrominated if sufficient hydride was used.Reactions of the bromoalkylbenzophenones with hydrazine derivatives yielded benzodiazepines.Treatment with hydriodic acid and red phosphorus converted 1‐phenyl‐isochroman into o‐(2‐iodoethyl)diphenylmethane while 4,4‐dimethyl‐1‐phenyl‐isochroman yielded 10,11‐dihydro‐10,10‐dimethyl‐5H‐dibenzo[a,d]cycloheptene and a compound (C13H10)n of unknown structure.