Abstract
l'iyyaz A Chughtaiw and Valadimir A, Bud.ylin** Reactions of (Indolyi-3) phenyliodonium Naltil with sodium nitrite have been investigated.. Effect of trifluorcacetate and tom:glace an counterion wat also studied. The mecha.niem of the reactions in discussed,
INTRODUCTION
Beringer and his colleagu.ea (1953) have provided exatu.pIen of reaetione of dieryliodonium smite with simpie inorganic anions which appear to involve only an SNAr (Nucleophilic Aromatic Substitution) reaction. For example. the reaction of diphenyliodonium bromide with sodium nitrite in aqueous solution gave nitrobenzene in 06% yield, while the reaction of phenyl-o-nitrophemylindo-Edina bromide with the same reagent afforded c-dinitrobenrene in 80.; yield. No benzene was reported to have been formed., ID the like manner, the rea-ction of ansymmetricaliy substituted diaryliodoninm salts with altrite Ion in aqueous acetate gave, in a, nueleophilic nitrolynis reaction, a mixture of corm, Ponditg nitroarenee (leh st. al, 1918), Similarly, Lubitkowski et al. (1081 reported that diphenyliodoniam tetrailuoroborates with sodium nitrite in aqua-diazano gave nitrobenzene in 72-76 yield and a aimilar reaction with phenyl-p-totyl-iodoniu.na tetrafluoroborate yielded a mixturc of nitrobenzene and p-uitrobenzeme in a ratio of 2,3:1, On the tither hand, aromatic hydrocar-bon formation was a major competing 0.:EictiOn +Ahen potaosika m cyanide %vas used as the inorganic salt thne suggentia:g a racliefd chain reaction. In order to gain some insight into the factors determining whether the reaction of diaryliodonium salt (having indolyi as a ligandi with potassium nit-rite will proceed mainly by an SNAr reaction or (presumably) by a radical chain ruction, we decided to investigate in some depth the reaotione of (Ind°. ly1-3) phenyliodonium tilt with potansiuln nitrite,
Department of Chemistry, University of Agriculture, Faisalabad. **Faculty of Chemistry, Moscow State University,. Moscow, USSR.
