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Paper | Regular issue | Vol 55, No. 1, 2001, pp.155-162
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9075
Reactions of 1,3-Dithiolane-2-thione and 1,3-Dithiole-2-thiones with 4-Phenyl-1,2,4-triazoline-3,5-dione(PTAD)

Juzo Nakayama,* Liting Zhao, Yoshiaki Sugihara, and Akihiko Ishii

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

Abstract

1,3-Dithiolane-2-thione (1) and 1,3-dithiole-2-thione (18a) reacted with 4-phenyl-1,2,4-triazoline-3-dione (PTAD) to provide betaines, 4-phenyl-1-[2-(1,3-dithiolanio)]urazolide (8) (79%) and 4-phenyl-1-[2-(1,3-dithiolio)]-urazolide (19a) (73%), respectively. A mechanism, involving three-membered ring formation by an electrophilic 1,2-addition of the PTAD nitrogen atom to the C=S bond, is proposed. Discussion on the structure of 8 is made in some detail based on the spectroscopic data and X-Ray crystallographic analysis.