Tetrahedron

Synthesis of (4-chlorophenyl)-(1-oxo-1λ 4-benzo [b] thien-2-yl) methanone and study of its reactivity towards sulfur-and oxygen-containing nucleophiles

P Pouzet, I Erdelmeier, PM Dansette, D Mansuy

Index: Pouzet, Pascale; Erdelmeier, Irene; Dansette, Patrick M.; Mansuy, Daniel Tetrahedron, 1998 , vol. 54, # 49 p. 14811 - 14824

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Citation Number: 11

Abstract

(4-Chlorophenyl)-(1-oxo-1λ4-benzo [b] thien-2-yl) methanone 2a was synthesized by oxidation of the corresponding benzo [b] thiophene derivative 2 with the oxidative system H 2O 2TFA. This benzo [b] thiophene sulfoxide undergoes Michael-type nucleophilic addition of sulfur-and oxygen-containing nucleophiles either under basic conditions leading to 2, 3- dihydro-3-substituted-benzo [b]-thiophene 1-oxides or in acidic media leading then to ...