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Communication | Regular issue | Vol 29, No. 7, 1989, pp.1233-1236
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4986
Synthesis of Novel Chiral2,3-Dihydro-1,3,4-thiadiazoles with Extremely High Optical Rotations: X-Ray Crystal Structure of (2R)-D-Mandelyl-5-methylthio-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

Kouhei Toyooka,* Yoshiyuki Takeuchi, Zenei Taira, and Seiji Kuboto

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan


The reaction of 4-bromobenzaldehyde methylthio (thiocarbonyl)-hydrazone with chiral 5-phenyl-1,3-dioxolane-2,4-dione in the presence of trifluoroacetic acid gave chiral 2-(4-bromophenyl)-3-mandelyl-2,3-dihydro-1,3,4-thiadiazoles with extremely high optical rotations; the absolute configuration of the 2,3-dihydro-1,3,4-thiadiazole (2) was established by single crystal X-ray analysis.