Direction of 3-bromothiophene acylation with succinyl chloride

In the reaction of 3-bromothiophene with succinyl chloride in the presence of AlCl 3 , a mixture of three isomeric dibromo-substituted 1,4-di(2-thienyl)butane-1,4-diones was formed. The main component was the unsymmetrical 1-(3-bromo-2-thienyl)-4-(4-bromo-2-thienyl)butane-1,4-dione rather than 1,4-d...

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Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 49; no. 3; pp. 386 - 391
Main Authors Smirnov, V. I., Afanas’ev, A. V., Prostakishin, I. S., Belen’kii, L. I.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.06.2013
Springer Nature
Springer
Subjects
Acylation
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Pharmacy
Physical Sciences
Science & Technology
succinyl chloride
3-bromothiophene
dibromo-1,4-di(2-thienyl)butane-1,4-diones
thiophene
acylation
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Summary:In the reaction of 3-bromothiophene with succinyl chloride in the presence of AlCl 3 , a mixture of three isomeric dibromo-substituted 1,4-di(2-thienyl)butane-1,4-diones was formed. The main component was the unsymmetrical 1-(3-bromo-2-thienyl)-4-(4-bromo-2-thienyl)butane-1,4-dione rather than 1,4-di-(3-bromo-2-thienyl)butane-1,4-dione expected according to the orientation rules.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-013-1258-5