9-Fluorenyl 9-(p-tolylsulfonyl)-9-fluorenyl disulfide: the unexpected product of the reaction of 9-bromofluorene and potassium p-toluenethiosulfonate and the …

…, L Kupczyk-Subotkowska

Index: Kice, John L.; Kutateladze, Tatiana G.; Kupczyk-Subotkowska, Lidia Journal of Organic Chemistry, 1991 , vol. 56, # 21 p. 6151 - 6155

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Citation Number: 3

Abstract

Reaction of potassium p-toluenethiosulfonate with 9-bromofluorene leads, not to the expected 9-fluorenyl p-toluenethiosulfonate (3), but rather to a product shown to be 9- fluorenyl9-(p-tolylsdfonyl)-9-fluorenyl disulfide (7, R= 9-fluorenyl)(eq 11). This disulfide of unusual structure is shown to arise as a result of the following reaction sequence:(a) initial formation of 3 (b) a facile elimination of 3 (due to the acidity of the 9-H), forming p- ...