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Note | Regular issue | Vol 68, No. 5, 2006, pp.1031-1041
Published online, 28th March, 2006
DOI: 10.3987/COM-06-10718
Synthesis and Structural Analysis of 3,6,8,11,16-Hexahydrodicyclopenta[c,h][1,6]dithiecin

Mitsunori Oda,* Yanmei Zhang, Nguyen Chung Thanh, Shu-ichi Hayashi, Shengli Zuo, and Shigeyasu Kuroda*

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi, Matsumoto, Nagano 390-0313, Japan

Abstract

The cycloaddition reaction of 3,6,9-trihydrocyclohepta[c][1,2]dithiin (5), prepared from 3,4-bis(bromomethyl)-1,3,5-cycloheptatriene (3) in two steps, with 3,4-dimethylene-1,5-cycloheptadiene (6) in the presence of boron trifluoride-etherate gave 3,6,8,11,16-hexahydrodicyclohepta[c,h][1,6]dithiecin (2). The temperature-dependent NMR study indicated that 2 possesses the fluxional tetrahydrodithiecin moiety in solution at room temperature. The X-Ray crystal structure analysis showed that 2 has an S-letter shape which was supported as the most stable conformer by DFT molecular orbital calculations.