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.[3]
(CH2S)3 + RLi → (CH2S)2(CHLiS) + RH
(CH2S)2(CHLiS) + R′Br → (CH2S)2(CHR′S) + LiBr
(CH2S)2(CHR′S) + H2O → R′CHO + ....
Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.
Trithiane is the parent of a class of heterocycles called trithianes, that formally result from substitution of various monovalentgroups 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.[5]
The conformation of trithianes has been well investigated.[6]
Referencesedit
^David R. Lide, ed. Handbook of Chemistry and Physics, 85th Edition, Internet Version 2005. CRC Press, 2005.
^Edema, Jilles J. H.; Hoogenraad, Marcel; Schoonbeek, Franck S.; Kellogg, Richard M.; Kooijman, Huub; Spek, Anthony L. (2010). "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". Recueil des Travaux Chimiques des Pays-Bas. 112 (6): 370–375. doi:10.1002/recl.19931120611.
^Breslow, David S.; Skolnik, Herman (2009). "C3S3 Ring Systems". Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2. Vol. 21. John Wiley & Sons. p. 689. ISBN978-0-470-18833-0.
January 01, 1970
trithiane, chemical, compound, with, formula, ch2s, this, heterocycle, cyclic, trimer, otherwise, unstable, species, thioformaldehyde, consists, membered, ring, with, alternating, methylene, bridges, thioether, groups, prepared, treatment, formaldehyde, with, . 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 2 1 3 5 Trithiane Names Preferred IUPAC name 1 3 5 Trithiane Other names Thioformaldehyde trimer Trimethylentrisulfide Trimethylene trisulfide Trithioformaldehyde 1 3 5 Trithiacyclohexane sym Trithiane Thioform s Trithiane Identifiers CAS Number 291 21 4 N 3D model JSmol Interactive image ChEBI CHEBI 39196 Y ChemSpider 8907 Y ECHA InfoCard 100 005 482 EC Number 206 029 7 PubChem CID 9264 UNII 4AM764YC6X Y CompTox Dashboard EPA DTXSID2059778 InChI InChI 1S C3H6S3 c1 4 2 6 3 5 1 h1 3H2 YKey LORRLQMLLQLPSJ UHFFFAOYSA N YInChI 1 C3H6S3 c1 4 2 6 3 5 1 h1 3H2Key LORRLQMLLQLPSJ UHFFFAOYAA SMILES S1CSCSC1 Properties Chemical formula C3H6S3 Molar mass 138 27 Appearance Colourless solid Density 1 6374 g cm3 1 Melting point 215 to 220 C 419 to 428 F 488 to 493 K Solubility in water Slightly soluble Solubility Benzene Hazards Occupational safety and health OHS OSH Main hazards Toxic T GHS labelling Pictograms Signal word Warning Hazard statements H319 Precautionary statements P264 P280 P305 P351 P338 P313 NFPA 704 fire diamond 110 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 3 CH2S 3 RLi CH2S 2 CHLiS RH CH2S 2 CHLiS R Br CH2S 2 CHR S LiBr CH2S 2 CHR S H2O R CHO 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 4 CH2S 3 9 Cl2 6 H2O 3 ClCH2SO2Cl 12 HCl Sample of sym trithiane Trithianes editTrithiane 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 5 The conformation of trithianes has been well investigated 6 nbsp References edit David R Lide ed Handbook of Chemistry and Physics 85th Edition Internet Version 2005 CRC Press 2005 Bost R W Constable E W sym Trithiane Organic Syntheses Collected Volume 2 p 610 1943 http orgsyn org Content pdfs procedures CV2P0610 pdf 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 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 Edema Jilles J H Hoogenraad Marcel Schoonbeek Franck S Kellogg Richard M Kooijman Huub Spek Anthony L 2010 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 Recueil des Travaux Chimiques des Pays Bas 112 6 370 375 doi 10 1002 recl 19931120611 Breslow David S Skolnik Herman 2009 C3S3 Ring Systems Multi Sulfur and Sulfur and Oxygen Five and Six Membered Heterocycles Part 2 Vol 21 John Wiley amp Sons p 689 ISBN 978 0 470 18833 0 Retrieved from https en wikipedia org w index php title 1 3 5 Trithiane amp oldid 1194905812, wikipedia, wiki, book, books, library,
