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Synthesis 1996; 1996(10): 1185-1187
DOI: 10.1055/s-1996-4354
short paper
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Novel Synthesis of Stable Furan and Thiophene o-Amino Thioaldehydes by Reaction of o-Azido Aldehydes with Hexamethyldisilathiane

Antonella Capperucci, Alessandro Degl’Innocenti1 , Maria Funicello, Patrizia Scafato, Piero Spagnolo2
  • 1Dipartimento di Chimica Organica, via G. Capponi, 9, I-50121 Firenze, Italy
  • 2Dipartimento di Chimica Organica ”A. Mangini”, Università di Bologna, viale Risorgimento 4, I-40100 Bologna, Italy
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Publication Date:
31 December 2000 (online)

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A new synthesis of monomeric o-amino thioaldehydes of thiophene, benzo[b]thiophene, furan and benzo[b]furan by reaction the corresponding o-azido aldehydes with hexamethyldisilathiane in neat acetonitrile and/or in methanol in the presence of hydrochloric acid at room temperature is reported.

Monomeric heteroaromatic o-amino thioaldehydes are obtained from o-azido aldehydes and hexamethyldisilathiane in MeCN or MeOH/HCl.