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The sodium/liquid ammonia cleavage of the dimethoxybenzenes and related substances, reported in large part by Birch in 1947, has been re-examined with use of improved techniques. Remarkable patterns of reactivity (e.g., ortho > meta >> para) that he described are confirmed and extended. They are agreeably rationalized by means of a simple, approximate adaptation from MO theory.
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Bunnett et al. (1996) studied this question.
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