Treatment of anthranilic acid with nitrous acid gives an intermediate, A, that contains

Chapter 20, Problem 20.43

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Treatment of anthranilic acid with nitrous acid gives an intermediate, A, that contains adiazonium ion and a carboxylate group. When this intermediate is heated in the pres-ence of furan, a bicyclic compound is formed. Propose a structural formula for com-pound A and a mechanism for the formation of the bicyclic product.

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