title: Fused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties.
abstract: A new general protocol for synthesis of fused 1,2,3-dithiazoles by the reaction of cyclic oximes with S₂Cl₂ and pyridine in acetonitrile has been developed. The target 1,2,3-dithiazoles fused with various carbocycles, such as indene, naphthalenone, cyclohexadienone, cyclopentadiene, and benzoannulene, were selectively obtained in low to high yields. In most cases, the hetero ring-closure was accompanied by chlorination of the carbocyclic moieties. With naphthalenone derivatives, a novel dithiazole rearrangement (15→13) featuring unexpected movement of the dithiazole ring from α- to β-position, with respect to keto group, was discovered. Molecular structure of 4-chloro-5H-naphtho[1,2-d][1,2,3]dithiazol-5-one 13 was confirmed by single-crystal X-ray diffraction. Electrochemical properties of 13 were studied by cyclic voltammetry and a complex behavior was observed, most likely including hydrodechlorination at a low potential.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia. konstantinova_ls@mail.ru.|Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia. konstantinova_ls@mail.ru.
authors.forename: Lidia S
authors.initials: LS
authors.lastname: Konstantinova
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia. ilay679@rambler.ru.
authors.forename: Ilia V
authors.initials: IV
authors.lastname: Baranovsky
authors.affiliation: N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia. irteg@nioch.nsc.ru.
authors.forename: Irina G
authors.initials: IG
authors.lastname: Irtegova
authors.affiliation: N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia. bagryan@nioch.nsc.ru.|Department of Natural Sciences, National Research University-Novosibirsk State University, 630090 Novosibirsk, Russia. bagryan@nioch.nsc.ru.
authors.forename: Irina Y
authors.initials: IY
authors.lastname: Bagryanskaya
authors.affiliation: N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia. shundrin@nioch.nsc.ru.|Department of Natural Sciences, National Research University-Novosibirsk State University, 630090 Novosibirsk, Russia. shundrin@nioch.nsc.ru.
authors.forename: Leonid A
authors.initials: LA
authors.lastname: Shundrin
authors.affiliation: N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090 Novosibirsk, Russia. zibarev@nioch.nsc.ru.|Department of Chemistry, National Research University-Tomsk State University, 634050 Tomsk, Russia. zibarev@nioch.nsc.ru.
authors.forename: Andrey V
authors.initials: AV
authors.lastname: Zibarev
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia. orakitin@ioc.ac.ru.|Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia. orakitin@ioc.ac.ru.
authors.forename: Oleg A
authors.initials: OA
authors.lastname: Rakitin
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D010091:Oximes; D013844:Thiazoles
keywords: X-ray diffraction; cyclic voltammetry; fused 1,2,3-dithiazoles; sulfur monochloride; synthesis