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Paper | Regular issue | Vol 78, No. 1, 2009, pp.103-115
Published online, 25th August, 2008
DOI: 10.3987/COM-08-11496
Synthesis and Sulfuration of 2’-Adamantylidene-9-benzonorbornenylidenee

Yoshiaki Sugihara,* Ayumi Kobiki, and Juzo Nakayama*

*Department of Chemistry, Faculty of Science, Saitama University, Urawa, Saitama 338-8570, Japan

Abstract

A novel alkene, 2’-adamantylidene-9-benzonorbornene 6, was synthesized from 2-adamantanone 7 in three steps resulting in a good overall yield. The alkene 6 reacted with elemental sulfur in refluxing o-Cl2C6H4 to give syn-thiirane 14, anti-thiirane 15, and 6. Almost the same ratio of the products was obtained when 14 or 15 was reacted with and without elemental sulfur under the same conditions. Sulfuration with Ph3CSCl in CH2Cl2 at -78 °C afforded 14, and that at room temperature furnished a 3:1 mixture of 14 and 15. In contrast, although the sulfuration with Ph3CSCl in CH2Cl2 at room temperature afforded 14 quantitatively, that at -78 °C gave 14 and 15 in 12 and 3% yields, respectively. Sulfuration by 1 molar equiv. of S2Cl2 or SCl2 afforded 14 and vic-dichloride 28.