Synthesis, Structure, and Ring Conversion of 1,2-Dithiete and Related Compounds

Autor:	Toshio Shimizu, Yukako Kobayashi, Kazuko Iwata, Nobumasa Kamigata, Hideyuki Murakami
Rok vydání:	1998
Předmět:	Solvent Cyclic compound chemistry.chemical_compound chemistry Silica gel Organic Chemistry Sulfuryl chloride Crystal structure Selectivity Dithiete Ring (chemistry) Medicinal chemistry
Zdroj:	The Journal of Organic Chemistry. 63:8192-8199
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo9806714
Popis:	3,4-Bis(methoxycarbonyl)-1,2-dithiete (6), 3,4,7,8-tetrakis(methoxycarbonyl)-1,2,5,6-tetrathiocin (8), and (Z,Z,Z,Z)-3,4,7,8,11,12,15,16-octakis(methoxycarbonyl)-1,2,5,6,9,10,13,14-octathiacyclohexadeca-3,7,11,15-tetraene (9) were synthesized by oxidation of titanocene dithiolene complex 4 with sulfuryl chloride, and the crystal structures of 6 and 8 were characterized by X-ray crystallographic analysis which revealed planar and twist geometries, respectively. Tetrathiocin 1, 11, and 12, and 16-membered cyclic compound 3 were also obtained by oxidation of the corresponding dithiolate or dithiolene complex. Dithiete 6 underwent tetramerization selectively to give 16-membered cyclic product 9 even at room temperature. Ring conversion reactions also proceeded among the 4-, 8-, and 16-membered unsaturated cyclic compounds possessing disulfide bonds under various conditions, such as in polar solvent or in the presence of silica gel. The ring-size selectivity of these ring conversion reactions was studied using...
Databáze:	OpenAIRE
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