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Facile Synthesis of 3-Nitro-2-substituted Thiophenes

O'Connor, CJ; Roydhouse, MD; Przybyl, AM; Wall, MD; Southern, JM; (2010) Facile Synthesis of 3-Nitro-2-substituted Thiophenes. J ORG CHEM , 75 (8) 2534 - 2538. 10.1021/jo902656y.

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Abstract

A new approach to 3-nitro-2-substituted thiophenes has been developed. Exposure of commercially available 1,4-dithane-2,5-diol to nitroalkenes in the presence of 20% triethylamine results in a tandem Michael intramolecular Henry reaction to form the corresponding tetrahydrothiophene. Subsequent microwave irradiation on acidic alumina in the presence of chloranil effects the solvent free dehydration and aromatization to form 3-nitro-2-substituted thiophenes cleanly and rapidly. A simple workup procedure removes the requirement for purification by chromatography in most cases.

Type:Article
Title:Facile Synthesis of 3-Nitro-2-substituted Thiophenes
DOI:10.1021/jo902656y
Keywords:FIELD-EFFECT TRANSISTORS, THIN-FILM TRANSISTORS, AMORPHOUS MOLECULAR MATERIALS, WILLARDIINE DERIVATIVES, CARBONYL-COMPOUNDS, SEMICONDUCTORS, OLIGOTHIOPHENES, PERFORMANCE, MICROWAVES, OLIGOMERS
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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