Thiophene, Benzo[b]thiophene and Dibenzo[b,d]thiophene as Precursors to Highly Conjugated Organosulfur Compounds

Claudio Bianchini; Andrea Meli

doi:10.1055/s-1997-3237

Synlett 1997; 1997(6): 643-649
DOI: 10.1055/s-1997-3237

account

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Thiophene, Benzo[b]thiophene and Dibenzo[b,d]thiophene as Precursors to Highly Conjugated Organosulfur Compounds

Claudio Bianchini^* , Andrea Meli

^*Istituto per lo Studio della Stereochimica ed Energetica dei Composti di Coordinazione, ISSECC-CNR - Via J. Nardi 39 - 50132 Firenze (Italy), Fax (55) 2428366; Bitnet bianchin@cacao.issecc.fi.cnr.it

Abstract

PDF Download All articles of this category

This account concerns the use of thiophenes (thiophene, benzo[b]thiophene and dibenzo[b,d]thiophene) to synthesize unusual organosulfur molecules, including α,β-unsaturated thioaldehydes, ylidenecyclohexadienethiones, α,β-unsaturated thioketones, butadienyl alkyl sulfides and o-(organylthio)styrenes, which are not easily accessible by usual organic chemistry methodologies. As a general procedure, thiophenes are cleaved by action of a metal fragment (Rh or Ir) to give C-S insertion products, which undergo regioselective electrophilic attack at either the metalated carbon or sulfur atoms depending on the nature of the electrophile. Subsequent carbonylation reactions in autoclaves liberate the organosulfur products from the metals, which are recovered as bis(carbonyl) complexes.

organosulfur compounds - thiophenes - C-C cleavage - rhodium

PDF (541 kb)