Abstract
Tetra- and Trialkylthiophenes 4–6 React with 2-Butynedinitrile in the Presence of 1 Equiv of Aluminum Chloride in Dichloromethane at 0 °C Via [2 + 2] Cycloaddition to 2-3.2.0] hepta-3,6-Diene-6,7-Dicarbonitriles 7–10 as the Major Products. Reaction of 4 and 5 Also Gave Small Amounts (4% and 6%) of 1,2-Benzenedicarbonitriles 11 and 12 Which Result from [4 + 2] Cycloaddition and Subsequent Extrusion of Sulfur. 4,5,6,7-Tetrahydro-1,3-Dimethylbenzo[C]thiophene (6) Reacts with 2-Butynedinitrile under the Same Conditions to Give an "Ene" Adduct (13) in Addition to the [2 + 2] Cycloadduct 10. 2,5-Dimethylthiophene (3) Gave a 2:1 Reaction Product 14, the Formation of Which Can Be Explained Via Friedel-Crafts Alkylation of 3 by the Initially Formed [2 + 2] Cycloadduct. the 2-3.2.0] hepta-3,6-Dienes 7–10 and the "Ene" Adduct 13 Show Intramolecular Charge-Transfer Absorptions in the UV Spectra. © 1982, American Chemical Society. All Rights Reserved.
Recommended Citation
Hall, R. H., den Hertog, H. J., & Reinhoudt, D. N. (1982). 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 1. Aluminum Chloride Catalyzed Thermal [2 + 2] Cycloaddition of 2-Butynedinitrile with Alkyl-Substituted Thiophenes. Journal of Organic Chemistry, 47(6), pp. 967-971. American Chemical Society.
The definitive version is available at https://doi.org/10.1021/jo00345a014
Department(s)
Business and Information Technology
International Standard Serial Number (ISSN)
1520-6904; 0022-3263
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2023 American Chemical Society, All rights reserved.
Publication Date
01 Jan 1982
