1,4-Oxathiane

1,4-Thioxane.png 120px 1,4-Oxathiane 1,4-Thioxane; p-Thioxane; 1-Oxa-4-thiacyclohexane 27596 15980-15-1 25685 240-117-6 2X66H33V2V DTXSID0065985 1S/C4H8OS/c1-3-6-4-2-5-1/h1-4H2 JBYHSSAVUBIJMK-UHFFFAOYSA-N C1CSCCO1 4 8 1 1 147.0 −17 2830 mg/kg oral rat 02 07 Warning 226 315 319 335 210 233 240 241 242 243 261 264 271 280 302+352 303+361+353 304+340 305+351+338 312 321 332+313 337+313 362 370+378 403+233 403+235 405 501 1,4-dioxane 1,4-Oxathiane is a heterocyclic compound containing one oxygen atom and one sulfur atom at opposite corners of a saturated six-membered ring. By systematic numbering, the oxygen atom is position number 1, sulfur is number 4, and positions 2, 3, 5, and 6 are carbon atoms. Production 1,4-Oxathiane can be produced from low cost ingredients by heating ethylene glycol or ethylene oxide with hydrogen sulfide. Alternate ways are to dehydrate bis(hydroxy ethyl) sulfide by heating with potassium hydrogen sulfate. These reactions also form 1,4-dithiane as a byproduct. The original 1912 preparation of 1,4-oxathiane involved iodoethyl ether with potassium sulfide in alcohol. A similar method used 2-chloroethyl ether. Reactions The sulfur atom in 1,4-oxathiane can undergo reaction as other substituted sulfides can. It can be oxidised to a sulfoxide with calcium hypochlorite or sodium periodate,10.1055/sos-SD-007-00192 Product Subclass 8: Aluminum Oxide (Alumina) Category 1, Organometallics 2004 9783131122117 Yamamoto or continuing to a sulfone. 400px It can react with ammonia to form diimines.10.1055/sos-SD-039-00922 Product Subclass 2: Cyclic Dialkyl Sulfones and Derivatives Category 5, Compounds with One Saturated Carbon Heteroatom Bond 2008 9783131189219 Kambe With elemental chlorine below 0 °C, 3-chloro-1,4-oxathiane is formed. Above 0 °C, 2,3-dichloro-1,4-oxathiane results and further chlorination yields 2,3,5,6-tetrachloro-1,4-oxathiane.Breslow David S. David S. Breslow Skolnik Herman Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles 2009 John Wiley & Sons 978-0-470-18833-0 823–828 https://books.google.com/books?id=CgRLJvZYBpYC&pg=PA828 en With hydrofluoric acid, 1,4-oxathiane is undergoes electrophilic fluorination to yield perfluoro-1,4-oxathiane: all eight hydrogen atoms are replaced with fluorine substituents, and also four fluorine atoms are attached to the sulfur atom. With elemental bromine in ether, an oxathianium salt is formed. In this an extra bromine atom bonds to the sulfur atom which gets a positive charge. To balance this, a bromide ion forms to make up a salt. Similarly iodine in acetic acid reacts to make 4-iodo-1,4-oxathianium iodide. Heating 1,4-oxathiane with ethyl iodide yields 4-ethyl-1,4-oxathianium iodide. References Category:Sulfur heterocycles Category:Oxygen heterocycles