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Recent Advances in the Chemistry of Thiophenes

1963; Elsevier BV; Linguagem: Inglês

10.1016/s0065-2725(08)60523-1

1557-8429

Salo Gronowitz,

Asymmetric Synthesis and Catalysis

Publisher Summary This chapter discusses the molecular structure and physical properties of thiophenes. The whole arsenal of spectroscopic and other physical methods are utilized to study the aromatic character of thiophene and the substituent effects in thiophenes. Metalation and halogen-metal interconversion reactions are shown to be of great utility in the preparation of substituted thiophenes. The chapter also discusses the spectroscopy of thiophenes and thermodynamic properties of thiophene 2-methylthiophene, and 3-methylthiophene. Different methods discussed for the preparation of thiophenes are ring-closure reactions, heterocyclic systems, 2-substituted compounds, and 3-substituted compounds. Comparison of the 2- and 3-positions of thiophene with benzene is provided. In the reactions of 2, 5-disubstituted thiophenes elimination of α-substituent occurs to a much greater extent than in the benzene series. Side-chain reactivity of thiophenes is also provided in the chapter. The reactions leading to the destruction of the thiophene aromaticity is discussed.