Oxathiols

Left to right: 3H-1,2-oxathiol, 5H-1,2-oxathiol, 1,3-oxathiol

Oxathiols form a class of substances in the field of heterocycles . They are 5-membered ring systems with exactly one sulfur and one oxygen heteroatom each, as well as a C = C double bond in the ring. There are therefore two basic structures of the oxathiol: the 1,2-oxathiol and the 1,3-oxathiol , with 1,2-oxathiol having two tautomers , depending on where the C = C double bond is located. Most of the research has been done on 1,3-oxathiol, 5H-1,2-oxathiol-2-oxide and 5H-1,2-oxathiol-2,2-dioxide.

meaning

1,2-Oxathiolane-2-oxides are of interest for the synthesis of α-β-unsaturated carbonyl compounds such as cinnamaldehyde , since they eliminate sulfur monoxide when heated , which leads to ring opening .

literature

• J. Alvarez-Builla, JJ Vaquero, J. Barluenga: Modern Heterocyclic Chemistry. Volume 2, Wiley-VCH Verlag & Co.KGaA, 2011, ISBN 978-3-527-33201-4 , pp. 966-980.
• DL Rakhmanklov, VV Zorin, FN Latypova, SS Zlotski, RA Karakhanov: In: Russian Chemical Reviews. Volume 52, 1983, p. 350.
• P. Wimmer: Methods of organic chemistry. Houben-Weyl, 1991.

Individual evidence

1. ↑ RFJ long Dries, FC De Schryver: PHOTO CHEMISTRY OF HETEROCYCLES. PART IV., PHOTOLYSIS OF THIETE-1,1-DIOXIDES . In: Tetrahedron Letters . tape 13 , no. 47 . Pergamon Press, Heverlee October 18, 1972, p. 4781-4784 .