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Dimethylsulfonio- and sulfo-de-hydrogenation on reaction of azuleno[2,1,8-ija]azulene (isopyrene) with the dimethyl sulfoxide-sulfur trioxide complex as reagent

✍ Scribed by Hans Cerfontain; Ankie Koeberg-Telder; Emanuel Vogel; Oswald Wilmes


Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
323 KB
Volume
113
Category
Article
ISSN
0165-0513

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✦ Synopsis


Abstract

Reaction of azuleno[2,1,8‐ija]azulene (isopyrene, 1) with SO~3~ in the presence of an excess of DMSO leads mainly to mono‐“dimethylsulfonio‐de‐hydrogenation” with formation of 5‐(dimethylsulfonio)isopyrene, the amount of initial sulfonation being relatively small. Subsequently, the 5‐(dimethylsulfonio)isopyrene is relatively slowly sulfo‐de‐hydrogenated to yield 5‐(dimethylsulfonio)isopyrene‐10‐sulfonic acid.