Standard Article

The Preparation of Thiophenes and Tetrahydrothiophenes

  1. Donald E. Wolf,
  2. Karl Folkers

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or006.09

Organic Reactions

Organic Reactions

How to Cite

Wolf, D. E. and Folkers, K. 2011. The Preparation of Thiophenes and Tetrahydrothiophenes. Organic Reactions. 6:9:410–468.

Author Information

  1. Merck & Co., Inc.

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

Thiophenes and tetrahydrothiophenes are discussed as separate major divisions in this chapter because there are significant differences in the general methods by which these two similar types of compounds are prepared. The general reactions that lead to the formation of thiophenes may be segregated in the following five general classifications (1) Reaction of the 1,4-difunctional compounds with sulfides; (2) reaction of unsaturated compounds with sulfides; (3) reaction of 1,2-difunctional compounds with thiodiacetic acid and esters; (4) reaction of aryl methyl ketones with sulfides; (5) miscellaneous cyclization reactions. Similarly the reactions that form tetrahydrothiophenes may be grouped into four general classifications: (1) Reaction of 1,4-difunctional compounds with sulfides; (2) Dieckmann cyclization; (3) Catalytic method; (4) miscellaneous methods. All of the above are discussed in this chapter.

Keywords:

  • thiophenes;
  • tetrahydrothiophenes;
  • sulfides;
  • succinic acids;
  • 1,4-Difunctional compounds;
  • 1,2-Difunctional compounds;
  • experimental procedures