Add time:07/15/2019         Source:sciencedirect.com

Publisher SummaryThis chapter deals with the chemistry of benzo[b]thiophene from the beginning of 1952 to June 30, 1968. Benzo[b]thiophene is available in semi-commercial quantities. At times, it is difficult to purchase, but it can be readily synthesized from thiophenol. Benzo[b]thiophenes can occur either in crude petroleum oil or in coal tar. The chapter explains the molecular structure and physical properties of benzo[b]thiophenes, such as molecular orbital treatment of benzo[b]thiophene, spectroscopy of benzo[b]thiophenes, physical measurements, and stereochemical properties of benzo[b]thiophenes. Benzo[b]thiophenes can be prepared by ring-closure reactions such as cyclization of (arylthio)acetaldehyde dialkyl acetals; cyclization of (arylthio)acetones and aryl phenacyl sulfides; cyclization of s-arylthioglycolic acids; cyclization of β-aryl-α-mercaptoacrylic acids and related compounds; Krollpfeiffer syntheses; from thiophenes; and benzo[b]thiophene-1,l-dioxides. The chapter also discusses the miscellaneous reactions and properties of benzo[b]thiophenes. The positive identification of the sulfur compounds in crude oils is a difficult problem often complicated by the lack of reference compounds. This difficulty has been overcome by hydrodesulfurization. A large number of benzo[b]thiophenes (amines, nitriles, carboxylic acids, and sulfonic acids) are now available by a variety of synthetic routes.

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