Sulfur monoxide transfer from peri-substituted trisulfide-2-oxides to dienes: substituent effects, mechanistic studies and application in thiophene synthesis

RS Grainger, B Patel, BM Kariuki, L Male…

Index: Grainger, Richard S.; Patel, Bhaven; Kariuki, Benson M.; Male, Louise; Spencer, Neil Journal of the American Chemical Society, 2011 , vol. 133, # 15 p. 5843 - 5852

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Citation Number: 20

Abstract

Three peri-substituted trisulfide-2-oxides are prepared by treatment of 1, 8-naphthalene dithiols with thionyl chloride and pyridine. The 1, 2, 3-trithiane-2-oxide ring adopts a sofa conformation in the solid state, with a pseudoaxial oxygen and evidence of ring strain (peri- interaction). Heating the trisulfide-2-oxides in the presence of a diene results in formal sulfur monoxide (SO) transfer to form unsaturated cyclic sulfoxides, along with a recyclable 1, 8- ...