1,3,5-Trithiane

Chemical compound changed changed 477204831 correct ?? 1,3,5-Trithiane.png 100px 1,3,5-trithiane-from-xtal-3D-balls.png 1,3,5-trithiane-from-xtal-3D-vdW.png 1,3,5-Trithiane Thioformaldehyde trimer, Trimethylentrisulfide, Trimethylene trisulfide, Trithioformaldehyde, 1,3,5-Trithiacyclohexane, sym-Trithiane, Thioform, s-Trithiane 1/C3H6S3/c1-4-2-6-3-5-1/h1-3H2 LORRLQMLLQLPSJ-UHFFFAOYAA correct chemspider 1S/C3H6S3/c1-4-2-6-3-5-1/h1-3H2 correct chemspider LORRLQMLLQLPSJ-UHFFFAOYSA-N changed ?? 291-21-4 correct FDA 4AM764YC6X 206-029-7 9264 correct chemspider correct EBI 39196 8907 S1CSCSC1 C3H6S3 138.27 Colourless solid 1.6374 g/cm3David R. Lide, ed. Handbook of Chemistry and Physics, 85th Edition, Internet Version 2005. CRC Press, 2005. 215 to 220 Slightly soluble Benzene Toxic (T) 1 1 0 07 Warning 319 264 280 305+351+338 313 1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.Bost, R. W.; Constable, E. W. "sym-Trithiane" Organic Syntheses, Collected Volume 2, p.610 (1943). http://orgsyn.org/Content/pdfs/procedures/CV2P0610.pdf Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.Seebach, D.; Beck, A. K. "Aldehydes From sym-Ttrithiane: n-Pentadecanal" Organic Syntheses, Collected Volume 6, p.869 (1988). http://orgsyn.org/Content/pdfs/procedures/CV6P0869.pdf (CH2S)3 + RLi → (CH2S)2(CHLiS) + RH (CH2S)2(CHLiS) + RBr → (CH2S)2(CHRS) + LiBr (CH2S)2(CHRS) + H2O → RCHO + .... Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above. It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride:Paquette, L. A.; Wittenbrook, L. S. "2-Chlorothiirane 1,1-Dioxide" Organic Syntheses, Collected Volume 5, p.231 (1973). http://orgsyn.org/Content/pdfs/procedures/CV5P0231.pdf (CH2S)3 + 9 Cl2 + 6 H2O → 3 ClCH2SO2Cl + 12 HCl thumb|left|200px|Sample of sym-trithiane. Trithianes Trithiane is the parent of a class of heterocycles called trithianes, that formally result from substitution of various monovalent groups for one or more of the hydrogen atoms. The species often arise from thiation of ketones and aldehydes. The incipient thioketones and thioaldehydes undergo trimerization. One example is 2,2,4,4,6,6-hexamethyl-1,3,5-trithiane, or trithioacetone, the trimer of thioacetone (propane-2-thione). Alternatively 1,3,5-trithiane can be deprotonated and alkylated to afford (SCH2)n(SCHR)3-n.10.1002/recl.19931120611 Alkylation of the SCS linkage. Towards lipophilic mono- and ditopic heavy-metal receptors containing trithiane building blocks. Molecular structure of cis-2,4,6-tribenzyl-1,3,5-trithiane 2010 Edema Jilles J. H. Hoogenraad Marcel Schoonbeek Franck S. Kellogg Richard M. Kooijman Huub Spek Anthony L. Recueil des Travaux Chimiques des Pays-Bas 112 6 370–375 The conformation of trithianes has been well investigated.Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2 21 Breslow David S. David S. Breslow Skolnik Herman C3S3 Ring Systems 689 978-0-470-18833-0 2009 John Wiley & Sons 220px References Category:Sulfur heterocycles Category:Six-membered rings