Synthesis of novel axially chiral cyclic benzopolysulfides |
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| Authors: | Ryu Sato Hidetoshi Ohta Tatsuya Yamamoto Shiduko Nakajo Satoshi Ogawa Ashraful Alam |
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| Affiliation: | Department of Chemical Engineering, Faculty of Engineering, Iwate University, Morioka 020-8551, Japan |
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| Abstract: | Novel axially chiral benzopentathiepins were synthesized by sulfurization of dithiastannole. Naphthyl moiety was introduced near the pentathiepin ring by Suzuki-Miyaura cross-coupling reaction. Pentathiepins were found as diastereomeric mixture. Rotational energy barrier for C-C bond was estimated by theoretical calculation. Energy barrier for the inversion of pentathiepin ring was experimentally determined by variable temperature 1H NMR. |
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| Keywords: | Axial chirality Diastereomer Naphthalene Pentathiepin Ring inversion |
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