A Convenient Synthesis of Thiophenes from β, γ-Epoxycarbonyl Compounds

References

• Cormier , R. A. , Grosshans , C. A. and Skibbe , S. L. 1988 . Synth. Commun , 18 : 677
   Web of Science ®Google Scholar
• Kang , K.-T. , Kang , U. J. S. , Hwang , S. S. and Jyung , K. K. 1994 . Synth. Commun , 24 : 2915
   Web of Science ®Google Scholar
• Kang , K.-T. and Kang , U. J. S. 1994 . Synth. Commun , 24 : 1507
   Web of Science ®Google Scholar
• Kang , K.-T. , Lee , J. C. and Lee , U. J. S. 1992 . Tetrahedron Lett , 33 : 4953
   Google Scholar
• Trost , B. M. , Buch , M. and Miller , M. L. 1988 . J. Org. Chem , 53 : 4887
   Google Scholar
• Kira , M. , Hino , T. and Sakurai , H. 1989 . Tetrahedron Lett , 30 : 1099
   Web of Science ®Google Scholar
• For example, 3i was readily isomerized to the corresponding conjugated enone: 1H NMR (a mixture of cis and trans isomers) δ 1.880, 1.885 (3H, d, J = 7.0 Hz), 1.965, 1.971 (3H, s), 6.400, 6.407 (1H, q, J = 7.0 Hz), 7.35–7.65 (5H, m).
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• 2-Isobutyl-4-chloromethylfuran was produced along with 5a 1H NMR δ 0.93 (6H, d, J = 6.6 Hz), 1.89–2.03 (1H, m), 2,45 (2H, d, J = 7.0 Hz), 4.43 (2H, s), 6.05 (1H, s), 7.30 (1H, s); 13C NMR δ 22.3, 27.8, 37.1, 37.6, 106.4, 122.7, 138.9, 157.1; MS m/e 174 (M+2, 11), 172 (M+, 32), 137 (25), 129 (100%)
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• 3a: 92%; 1H NMR δ 0.91 (6H, d, J = 6.6 Hz), 2.02–2.22 (1H, m), 2.33 (2H, d, J = 6.6 Hz), 3.28 (2H, s), 4.10 (2H, s), 5.00 (1H, s), 5.28 (1H, s). 4a: 85%; 1H NMR δ 0.90 (6H, d, J = 6.4 Hz), 2.02–2.22 (1H, m), 2.30 (2H, d, J = 6.4 Hz), 2.55 (1H, d, J = 17.4 Hz), 2.75 (1H, d, J = 4.4 Hz), 2.84 (1H, d, J = 4.4 Hz), 3.15 (1H, d, J = 17.4 Hz), 3.52 (1H, d, J = 11.8 Hz), 3.82 (1H, d, J = 11.8 Hz). 5a: 73%
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