Abstract
The 2-3.2.0] hepta-3,6-Dienes 1–7 Extrude Sulfur in Solution at 285 °C to Give the 1,2-Benzenedicarbonitriles 8–12 in Yields of 42–56%. 5-(1,1-Dimethylethyl)-3,6-Dimethyl-2-3.2.0] hepta-3,6-Diene-1,7-Dicarbonitrile (6) Reacts at 140 °C to Give a Mixture of the Cope-Rearranged Isomer 13, the 1,2-Benzenedicarbonitrile 11, and possibly a 3a,6a-Dihydrothieno[3,2-B] thiophene (14). Reaction of 2a,5,6,7,8,8a-Hexahydro-2a,4-Dimethylbenzo[C]cyclobuta[B]thiophene-L,2-Dicarbonitrile (15) at 140 °C Gives a Mixture of De8ulfurated (16) and Sulfureted (17) Products in Yields of 88% and 70%, Respectively. Single-Crystal X-Ray Analysis Proved the 3a,6,7,8,9,9a-Hexahydrothieno[3,2-B][2]benzothiophene Structure (17). the Possible Mechanism of the Insertion of Sulfur in the Carbon-Carbon Single Bond of 15 is Discussed. © 1982, American Chemical Society. All Rights Reserved.
Recommended Citation
Hall, R. H., den Hertog, H. J., Reinhoudt, D. N., Harkema, S., van Hummel, G. J., & Uiterwijk, J. W. (1982). 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes. 3. Desulfuration and Sulfuration of 2-Thiabicyclo[3.2.0]hepta-3,6-Dienes and X-Ray Crystal Structure of 3a,6,7,8,9,9a-Hexahydro-3a,5-Dimethylthieno[3,2-B][2]benzothiophene-2,3-Dicarbonitrile. Journal of Organic Chemistry, 47(6), pp. 977-982. American Chemical Society.
The definitive version is available at https://doi.org/10.1021/jo00345a016
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
