O'Connor, CJ and Roydhouse, MD and Przybyl, AM and Wall, MD and 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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