When tricyclic cyclooctyne derivative A reacts with benzyl azide (CeHsCH2N3), a [3+2] cycloaddition occurs between the alkyne and the azide (called a click reaction) to install a new five-membered heterocycle. N=N=N Ph Ph- „N +C A B (a) Propose a plausible mechanism for the formation of B. (b) Compounds B and C are constitutional isomers that are formed in roughly equal amounts. Draw the structure of compound C.

When tricyclic cyclooctyne derivative A reacts with benzyl azide (CeHsCH2N3), a [3+2] cycloaddition occurs between the alkyne and the azide (called a click reaction) to install a new five-membered heterocycle. N=N=N Ph Ph- „N +C A B (a) Propose a plausible mechanism for the formation of B. (b) Compounds B and C are constitutional isomers that are formed in roughly equal amounts. Draw the structure of compound C.

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

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.29P

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