The Journal of Organic Chemistry

Stereochemistry and mechanism of electrophilic additions to tricyclo [4.2. 2.02, 5] deca-3, 7-diene derivatives

G Mehta, PN Pandey

Index: Mehta,G.; Pandey,P.N. Journal of Organic Chemistry, 1975 , vol. 40, p. 3631 - 3637

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Citation Number: 17

Abstract

Electrophilic addition of iodine azide, mercuric acetate, nitrosyl chloride, and diborane to tricyclo-[4.2. 2.02 r5] deca-3, 7-diene derivatives 2, 4, and 5 is described. Reaction of iodine azide with diester 2 furnishes a syn azido iodide 6. On the other hand, IN3 addition to 4 and 5 in acetonitrile solvent results in transannular solvent participation and tetrazoles 8 and 10 are formed via Hassner-Ritter reaction. In methylene chloride solvent dienes 4 and 5 ...