Iododediazoniation of Arenediazonium Salts Accompanied by Aryl Radical Ring Closure
Treatment of o-(allyloxy)benzenediazonium tetrafluoroborate (1a) 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 (1b-i) containing suitable unsaturated side chains behave similarly, but those (1l,1m) in which there is an N-allylsulfonamido group yield mainly products formed by endo cyclization.The diazonium salts 1j and 1k do not give cyclized products.Factors affecting the mechanism, rates, and regiochemistry of the reaction are discussed.
Beckwith, Athelstan L. J.,Meijs, Gordon F.
p. 1922 - 1930
(2007/10/02)
Mechanistic and Kinetic Studies on the Iododediazoniation Reaction
Treatment of the diazonium salt 1 with sodium iodide in acetone gives a mixture of uncyclized (4) and cyclized (5) iododediazoniation products, the relative yields of which vary with the amount of added iodine but are independent of iodide concentration.T
Abeywickrema, Anil N.,Beckwith, Athelstan L. J.
p. 2568 - 2571
(2007/10/02)
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