The Journal of Organic Chemistry

Iododediazoniation of arenediazonium salts accompanied by aryl radical ring closure

ALJ Beckwith, GF Meijs

Index: Beckwith, Athelstan L. J.; Meijs, Gordon F. Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 1922 - 1930

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Citation Number: 92

Abstract

Treatment of o-(ally1oxy) benzenediaonium tetrafluoroborate (la) with sodium iodide in acetone affords the cyclized iodide 2a in good yield by a mechanism involving the generation and exo cyclization of the aryl radical 6a. Other diazonium salts (lb-i) containing suitable unsaturated side chains behave similarly, but those (11, lm) in which there is an N- allylsulfonamido group yield mainly products formed by endo cyclization. The diazonium ...