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Updated: Jun 14, 2026
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
[3.3]Dithia-bridged cyclophanes featuring a thienothiophene ring: synthesis, structures and conformational analysis
Sabir H Mashraqui1, Yogesh Sanghvikar, Shailesh Ghadhigaonkar
1Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz E, Mumbai 400 098. sh_mashraqui@yahoo.com
Abstract:
The synthesis of [3.3]dithia-bridged cyclophanes 7, 9 and 11 incorporating a fused heterocycle, thieno[2,3-b]thiophene is described. The structures are established by ¹H NMR analysis and, in the case of 11, also by single crystal X-ray crystallography. Conformational analysis by variable temperature NMR suggests that cyclophanes 7, 9 and 11 exhibit conformationally rigid bridges and rings at least up to 130° C. Energy minimization of 11 revealed anti-11 to be the most stable conformation. Although, the computed energy difference between the most stable conformation anti-11 and the next higher energy conformation syn-anti-11 is only 2.98 kJ/mol, it is intriguing that 11 does not exhibit thia-bridge inversion even at elevated temperatures.
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