Peculiarities of the behavior of succinyl dichloride in Friedel-Crafts reaction with thiophenes

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 46; no. 10; pp. 1199 - 1207
• Main Authors: Smirnov, V. I, Afanas'ev, A. V, Belen'kii, L. I
• Format: Journal Article
• Language: English
• Published: Boston Boston : Springer US 2011; Springer US; Springer Nature; Springer
• Subjects: 1,4-(2-thienyl)butane-1,4-diones; 4,4-di(2-thienyl)but-3-enoic acids; 4,4-di(2-thienyl)butyrolactones; 4-oxo-4-(2-thienyl)butyric acids; Acylation; Bisphenol-A; Chemical properties; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Electrical conductivity; Organic Chemistry; Pharmacy; Physical Sciences; Saturated fatty acids; Science & Technology; Substitution reactions; succinyl dichloride; Thiophene; thiophenes; 4,4-di(2-thienyl)butyrolactones; thiophenes; 4,4-di(2-thienyl)but-3-enoic acids; succinyl dichloride; 4-oxo-4-(2-thienyl)butyric acids; 1,4-(2-thienyl)butane-1,4-diones; acylation; ALKYLATION; BETA-AROYLPROPIONIC ACIDS; GRIGNARD REAGENTS; ESTERS; ANHYDRIDE; EQUIVALENT
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-011-0653-z

The reactions of thiophene, 2-methyl-, and 2-bromothiophene with succinyl dichloride in the presence of AlCl₃, TiCl₄, and SnCl₄ have been studied. The effect of the acylation conditions, the relative amounts and nature of the Lewis acid on the ratio and yields of the 1,4-di(2-thienyl)-1,4-diones and 4-oxo-4-(2-thienyl)butyric acids formed have been demonstrated. Under the reaction conditions, the formation of 4,4-di(2-thienyl)but-3-enoic acids (the main products in many cases) and also 4,4-di(2-thienyl)-butyrolactones was demonstrated.