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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![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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F96341549-5d0c-4ccf-81a8-964a022132be%2F1a445a0f-914f-4f73-99e4-5aeaa3aee996%2Flzy0qbb.jpeg&w=3840&q=75)
Transcribed Image Text: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
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