Treatment of anthranilic acid with nitrous acid gives an intermediate, A, that contains a diazonium ion and a carboxylate group. When this intermediate is heated in the pres- ence of furan, a tricyclic compound is formed. Propose a structural formula for com- pound A and a mechanism for the formation of the tricyclic product. COOH NANO, HCI + CO, + N2 NH2 Anthranilic acid

Treatment of anthranilic acid with nitrous acid gives an intermediate, A, that contains a diazonium ion and a carboxylate group. When this intermediate is heated in the pres- ence of furan, a tricyclic compound is formed. Propose a structural formula for com- pound A and a mechanism for the formation of the tricyclic product. COOH NANO, HCI + CO, + N2 NH2 Anthranilic acid

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.43P

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