キハラ ノブヒロ   Kihara Nobuhiro
  木原 伸浩
   所属   神奈川大学  理学部 化学科
   職種   教授
言語種別 英語
発行・発表の年月 1995/01
形態種別 学術雑誌
査読 査読あり
標題 Preparation of 1,3-Oxathiolane-2-thiones by the Reaction of Oxirane and Carbon Disulfide
執筆形態 共著
掲載誌名 J. Org. Chem.
巻・号・頁 60(2),pp.473-475
著者・共著者 Nobuhiro Kihara, Yuichi Nakawaki, and Takeshi Endo
概要 The reaction of I with 1.2 equiv. of CS2 at room temp. in THF in the presence of NaI afforded II as the major product. The reactions of various oxiranes and CS2 were examd. using LiBr as a catalyst in THF. Monosubstituted and gem-disubstituted oxiranes gave desired dithiocarbonates in high yields without the formation of possible side-products. It is noteworthy that trans-III was obtained as a single product from IV. The stereochem. obsd. for III indicates that SN2 inversion on the oxirane ring occurred once. The most plausible mechanism , i.e., reaction of xanthate anion with oxirane accompanied by SN2 inversion and subsequent intramol cyclocondensation is illustrated and discussed.
DOI 10.1021/jo00107a034
ISSN 0022-3263