3,4-Didehydrothiophene Precursors Useful for the Synthesis of 3,4-Disubstituted thiophenes

Thiophene rings are a common structural unit in many natural and synthetic molecules with possible applications like electronic materials and pharmaceuticals. 3,4-Didehydrothiophene is considered difficult to synthesize. Phenyl[4-(trimethylsilyl)thiophen-3-yl]iodonium triflate (1) has been reported as a precursor.^1,2) The addition of potassium fluoride to a dichloromethane solution of 1, 18-crown 6-ether and furan forms 3,4-didehydrothiophene in situ. This intermediate is trapped by furan to give 4,7-dihydro-4,7-epoxybenzo[c]thiophene (2).¹⁾

Related Products

P2097

Phenyl[4-(trimethylsilyl)thiophen-3-yl]iodonium Triflate

C0860

18-Crown 6-Ether

F0074

Furan

References

• 1) 3,4-Didehydrothiophene: Generation, Trapping Reactions, and Ab Initio Study
  • X. S. Ye, W. K. Li, H. N. C. Wong, J. Am. Chem. Soc. 1996, 118, 2511.
• 2) Synthetic Applications of 3,4-Bis(trimethylsilyl)thiophene: Unsymmetrically 3,4-Disubstituted Thiophenes and 3,4-Didehydrothiophene
  • X. S. Ye, H. N. C. Wong, J. Org. Chem. 1997, 62, 1940.

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