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■ 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.