HAHN, HG CHANG, KH LEE, WS 2024-01-21T20:40:46Z 2024-01-21T20:40:46Z 2021-09-02 1995-05-01 0385-5414 https://pubs.kist.re.kr/handle/201004/145082 The preparation of isomeric dihydro-1,4-oxathiin (3) from the dihydro-1,4-oxathiin (1) via dichloro-1,4-oxathiane (4) is described. Chlorination of 1 followed by treatment of the resulting dichloride (4) with aqueous acetone gave dihydroxy-1,4-oxathiin (5). The solvolysis to produce intermediate chlorohydrin (11) was favored relative to elimination reaction to give exomethylene compound (8). Dehydration of 5 followed by reduction afforded alpha-hydroxy-1,3-oxathiolane (2) which is a key compound to prepare the isomeric dihydro-1,4-oxathiin (3). The reason for more facile displacement of chlorine at C-2 in comparison with that at C-3 in 4 was also discussed. English ELSEVIER SCIENCE BV CONVERSION OF DIHYDRO-1,4-OXATHIIN-3-CARBOXAMIDE TO THE ISOMERIC DIHYDRO-1,4-OXATHIIN-2-CARBOXAMIDE Article 10.3987/COM-94-6944 1 HETEROCYCLES, v.41, no.5, pp.921 - 930 HETEROCYCLES 41 5 921 930 scie scopus A1995QW54900007 2-s2.0-0344321984 Chemistry, Organic Chemistry Article