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Paper | Special issue | Vol 93, No. 2, 2016, pp.714-722
Published online, 30th November, 2015
DOI: 10.3987/COM-15-S(T)62
Guaiazulenopentathiepin and Related Compounds: Reactions of Guaiazulene with Reactive Sulfuration Reagents

Ohki Sato,* Takahito Saito, Mana Iwase, and Atsushi Sakai

*Department of Chemistry, Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570 , Japan


Guaiazulene reacted with reactive sulfuration reagents to give guaiazulenopentathiepin together with a 1,2-dithiin compound and a mixture of bis(guaiazulyl)sulfides. The yield of the pentathiepin was improved by the reaction with the reagent prepared from sulfur chloride and imidazole in a molar ratio of one to two. Reduction of the pentathiepin and the successive reaction with N,N’-(thio)carbonyldiimidazoles afforded 2-(thi)oxo-1,3-dithioles.