Skip to main content
Log in

An efficient, one-pot synthesis of trithiocarbonates from alcoholic tosylates using the Cs2CO3/CS2 system

  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A single-step novel protocol for the preparation of symmetrical trithiocarbonates from a corresponding variety of primary, secondary, and tertiary alcoholic tosylates using the Cs2CO3/CS2 system, was developed. This protocol is mild and more efficient than the reported methods.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • M Gulea S Masson (2004) Top Curr Chem 250 257

    Google Scholar 

  • A Ishii J Nakayama (2005) Top Curr Chem 251 181 Occurrence Handle1:CAS:528:DC%2BD2MXmsV2ntL8%3D

    CAS  Google Scholar 

  • P Metzer (1996) Pure Appl Chem 68 863 Occurrence Handle10.1351/pac199668040863

    Article  Google Scholar 

  • B Quiclet-Sire SZ Zard (2006) Top Curr Chem 252 201 Occurrence Handle10.1007/128_029 Occurrence Handle1:CAS:528:DC%2BD28XmtVOjs70%3D

    Article  CAS  Google Scholar 

  • EZ Kipershlak AB Pakshver (1978) Fibre Chem 9 458 Occurrence Handle10.1007/BF00546443

    Article  Google Scholar 

  • YI Gevaza VI Staninets (1986) Chem Heterocycl Comp 22 231 Occurrence Handle10.1007/BF00514985

    Article  Google Scholar 

  • S Chander (2003) Int J Min Process 72 141 Occurrence Handle10.1016/S0301-7516(03)00094-2 Occurrence Handle1:CAS:528:DC%2BD3sXnt1Cgu7Y%3D

    Article  CAS  Google Scholar 

  • JD Miller J Li JC Davidtz F Vos (2005) Miner Eng 18 855 Occurrence Handle10.1016/j.mineng.2005.02.011 Occurrence Handle1:CAS:528:DC%2BD2MXmt1aqurY%3D

    Article  CAS  Google Scholar 

  • Y Zhang P Talalay (1994) Cancer Res 54 1976

    Google Scholar 

  • RR Chirumamilla R Marchant P Nigam (2001) J Chem Technol Biot 76 123 Occurrence Handle10.1002/jctb.337 Occurrence Handle1:CAS:528:DC%2BD3MXht1Skt78%3D

    Article  CAS  Google Scholar 

  • Jesberger M, Davis TP, Barner L (2003) Synthesis:1929

  • WO Foye J Mickles RN Duvall JR Marshall (1963) J Med Chem 6 509 Occurrence Handle10.1021/jm00341a008 Occurrence Handle1:CAS:528:DyaF3sXksFCiu7w%3D

    Article  CAS  Google Scholar 

  • I Kawamoto R Endo S Sugahara (1986) J Antibiotics 39 1551 Occurrence Handle1:CAS:528:DyaL1cXkt1alu7c%3D

    CAS  Google Scholar 

  • NM Slavachevskaya NS Tsepora YE Strelnikov IA Belen’Kaya (1979) Pharm Chem J 13 591

    Google Scholar 

  • S Sadanobu M Watanabe C Nakamura M Tezuka (1999) J Toxicol Sc 24 375 Occurrence Handle1:CAS:528:DC%2BD3cXhsFyisbY%3D

    CAS  Google Scholar 

  • F Dehmel T Ciossek T Maier S Weinbrenner B Schmidt M Zoche T Beckers (2007) Bio-Org Med Chem Lett 17 4746 Occurrence Handle10.1016/j.bmcl.2007.06.063 Occurrence Handle1:CAS:528:DC%2BD2sXos1ansLY%3D

    Article  CAS  Google Scholar 

  • JD Dignam RM Levovitz RG Roeder (1983) Nucleic Acid Res 11 1475 Occurrence Handle10.1093/nar/11.5.1475 Occurrence Handle1:CAS:528:DyaL3sXhslCit74%3D

    Article  CAS  Google Scholar 

  • D Wegener F Wirsching D Riester A Schwienhorst (2003) Chem Biol 10 61 Occurrence Handle10.1016/S1074-5521(02)00305-8 Occurrence Handle1:CAS:528:DC%2BD3sXps1Skuw%3D%3D

    Article  CAS  Google Scholar 

  • J O’Brian I Wilson T Orton F Pognan (2000) Eur J Biochem 267 5421 Occurrence Handle10.1046/j.1432-1327.2000.01606.x

    Article  Google Scholar 

  • Abbas M, Westermann B, Voelter W (2007) ARKIVOC:329

  • SG Spain MI Gibson NR Cameron (2007) J Polym Sci Pol Chem 45 2059 Occurrence Handle10.1002/pola.22106 Occurrence Handle1:CAS:528:DC%2BD2sXlsV2mtL8%3D

    Article  CAS  Google Scholar 

  • MT Leysen G Roybrouck HVD Voorde (1974) Allergy 29 455 Occurrence Handle10.1111/j.1398-9995.1974.tb01665.x Occurrence Handle1:CAS:528:DyaE2MXksFCmsb8%3D

    Article  CAS  Google Scholar 

  • CO Knowels (1978) Environ Health Persp 14 93 Occurrence Handle10.2307/3428366

    Article  Google Scholar 

  • DJ Johnson V Amarnath K Amarnath H Valentine WM Valentine (2003) Toxicol Sci 76 65 Occurrence Handle10.1093/toxsci/kfg226 Occurrence Handle1:CAS:528:DC%2BD3sXosVeqs78%3D

    Article  CAS  Google Scholar 

  • M Gulea S Masson (2004) Top Curr Chem 250 257

    Google Scholar 

  • A Ishii J Nakayama (2005) Top Curr Chem 251 181 Occurrence Handle1:CAS:528:DC%2BD2MXmsV2ntL8%3D

    CAS  Google Scholar 

  • P Metzer (1996) Pure Appl Chem 68 863 Occurrence Handle10.1351/pac199668040863

    Article  Google Scholar 

  • B Quiclet-Sire SZ Zard (2006) Top Curr Chem 252 201 Occurrence Handle10.1007/128_029 Occurrence Handle1:CAS:528:DC%2BD28XmtVOjs70%3D

    Article  CAS  Google Scholar 

  • Iqbal SM, Owen LN (1960) J Chem Soc:1030

  • Anisuzzaman AKM, Owen LN (1996) Chem Commun:16

  • Wuts PGM, Greene TW (2006) Protecting Groups in Organic Synthesis. John Wiley & Sons

  • RTA Mayadunne E Rizzardo J Chiefari J Kristina G Moad A Postama SH Thang (2000) Macromolecules 33 243 Occurrence Handle10.1021/ma991451a Occurrence Handle1:CAS:528:DC%2BD3cXhtlWgtA%3D%3D

    Article  CAS  Google Scholar 

  • JT Lai D Filla R Shea (2002) Macromolecules 35 6754 Occurrence Handle10.1021/ma020362m Occurrence Handle1:CAS:528:DC%2BD38XlslKisr8%3D

    Article  CAS  Google Scholar 

  • AS Duwez P Guillet C Colard JF Gohy CA Fustin (2006) Macromolecules 39 2729 Occurrence Handle10.1021/ma0602829 Occurrence Handle1:CAS:528:DC%2BD28XivVelurs%3D

    Article  CAS  Google Scholar 

  • R Wang CL McCormick AB Lowe (2005) Macromolecules 38 9518 Occurrence Handle10.1021/ma050669w Occurrence Handle1:CAS:528:DC%2BD2MXhtVyjt7rL

    Article  CAS  Google Scholar 

  • A Postama TP Davis G Li G Moad MS O’Shea (2006) Macromolecules 39 5307 Occurrence Handle10.1021/ma0604338 Occurrence Handle1:CAS:528:DC%2BD28Xms1Kntbw%3D

    Article  CAS  Google Scholar 

  • MF Ali S Abbas (2006) Fuel Process Technol 87 573 Occurrence Handle10.1016/j.fuproc.2006.03.001 Occurrence Handle1:CAS:528:DC%2BD28XlsFCmu78%3D

    Article  CAS  Google Scholar 

  • ON Anand V Kumar AK Singh RPS Bist (2007) Lubrication Sci 19 159 Occurrence Handle10.1002/ls.35 Occurrence Handle1:CAS:528:DC%2BD2sXpslOktr4%3D

    Article  CAS  Google Scholar 

  • Degani L, Fochi R, Gatti A, Regondi V (1986) Synthesis:894

  • W Choi F Sanda T Endo (1998) Macromolecules 31 2454 Occurrence Handle10.1021/ma971701s Occurrence Handle1:CAS:528:DyaK1cXislSgtrY%3D

    Article  CAS  Google Scholar 

  • W Choi F Sanda T Endo (1998) Macromolecules 31 9093 Occurrence Handle10.1021/ma9805102 Occurrence Handle1:CAS:528:DyaK1cXnt12isbg%3D

    Article  CAS  Google Scholar 

  • W Choi F Sanda T Endo (2000) Heterocycles 52 125 Occurrence Handle1:CAS:528:DC%2BD3cXis1OqsQ%3D%3D Occurrence Handle10.3987/COM-99-S41

    Article  CAS  Google Scholar 

  • N Nemoto F Sanda T Endo (2000) Macromolecules 33 7229 Occurrence Handle10.1021/ma000760u Occurrence Handle1:CAS:528:DC%2BD3cXmtlKrsbw%3D

    Article  CAS  Google Scholar 

  • F Sanda T Shinjo W Choi T Endo (2001) Macromol Rapid Commun 22 363 Occurrence Handle10.1002/1521-3927(20010301)22:5<363::AID-MARC363>3.0.CO;2-C Occurrence Handle1:CAS:528:DC%2BD3MXis1egsrs%3D

    Article  CAS  Google Scholar 

  • S Erima N Pradhan (2003) Comptes Rendus Chemie 6 1035 Occurrence Handle10.1016/j.crci.2003.08.002 Occurrence Handle1:CAS:528:DC%2BD3sXoslOgt7o%3D

    Article  CAS  Google Scholar 

  • H Yekeler M Yekeler (2004) Appl Surf Sci 236 435 Occurrence Handle10.1016/j.apsusc.2004.05.079 Occurrence Handle1:CAS:528:DC%2BD2cXms1Oisrs%3D

    Article  CAS  Google Scholar 

  • M Porento P Hirra (2002) Theor Chim Acta 107 200 Occurrence Handle1:CAS:528:DC%2BD38XksVymtLo%3D

    CAS  Google Scholar 

  • YR Guo QJ Pan GN Fang ZM Liu (2005) Chem Phy Lett 413 59 Occurrence Handle10.1016/j.cplett.2005.06.086 Occurrence Handle1:CAS:528:DC%2BD2MXps12qtbw%3D

    Article  CAS  Google Scholar 

  • EZ Kipershlak AB Pakshwer EB Kostikobe (1978) Fibre Chem 10 156 Occurrence Handle10.1007/BF00556336

    Article  Google Scholar 

  • W Foye JR Marshall J Mickles (2006) J Pharm Sci 52 406 Occurrence Handle10.1002/jps.2600520422

    Article  Google Scholar 

  • Bianchini C, Innocenti P, Meli M (1983) J Chem Soc Dalton Trans:1977

  • JP Fackler WC Siedel (1969) Inorg Chem 8 1631 Occurrence Handle10.1021/ic50078a012 Occurrence Handle1:CAS:528:DyaF1MXksFKitbo%3D

    Article  CAS  Google Scholar 

  • M El-khateeb A Roller (2007) Polyhedron 26 3920 Occurrence Handle10.1016/j.poly.2007.04.010 Occurrence Handle1:CAS:528:DC%2BD2sXpt1Clu7g%3D

    Article  CAS  Google Scholar 

  • P Metzner (1996) Pure Applied Chem 68 863 Occurrence Handle10.1351/pac199668040863 Occurrence Handle1:CAS:528:DyaK28XjslyitLc%3D

    Article  CAS  Google Scholar 

  • C Leriverend P Metzner A Capperucci A Degl’lnnocenti (1997) Tetrahedron 53 1323 Occurrence Handle10.1016/S0040-4020(96)01071-X Occurrence Handle1:CAS:528:DyaK2sXhtFOnsbc%3D

    Article  CAS  Google Scholar 

  • I El-Sayed KMH Hilmy SM El-Kousy A Fischer HS Slem (2003) Phosphorus Sulfur Silicon 178 2403 Occurrence Handle10.1080/714040954 Occurrence Handle1:CAS:528:DC%2BD3sXosVCjsrg%3D

    Article  CAS  Google Scholar 

  • DJ Martin CC Greco (1968) J Org Chem 33 1275 Occurrence Handle10.1021/jo01267a089 Occurrence Handle1:CAS:528:DyaF1cXos1ChtA%3D%3D

    Article  CAS  Google Scholar 

  • A Oliva A Molinari L Sanchez (1998) Synth Commun 28 3381 Occurrence Handle10.1080/00397919808004445 Occurrence Handle1:CAS:528:DyaK1cXls1GltLc%3D

    Article  CAS  Google Scholar 

  • U Jordis M Rudolf (1984) Phosphorus Sulfur Silicon 19 279 Occurrence Handle10.1080/03086648408077590 Occurrence Handle1:CAS:528:DyaL2cXmtFWjtL4%3D

    Article  CAS  Google Scholar 

  • EJ Corey FA Carey RAE Winter (1965) J Am Chem Soc 87 934 Occurrence Handle10.1021/ja01082a057 Occurrence Handle1:CAS:528:DyaF2MXot1WhsA%3D%3D

    Article  CAS  Google Scholar 

  • K Rasheed JD Warkentin (1980) J Org Chem 45 4041 Occurrence Handle10.1021/jo01308a020 Occurrence Handle1:CAS:528:DyaL3cXls1yitLk%3D

    Article  CAS  Google Scholar 

  • EJ Corey G Markl (1967) Tetrahedron Lett 8 3201 Occurrence Handle10.1016/S0040-4039(01)89899-3

    Article  Google Scholar 

  • M Chandrasekharam L Bhat H Ila H Junjappa (1993) Tetrahedron Lett 34 6439 Occurrence Handle10.1016/0040-4039(93)85065-5 Occurrence Handle1:CAS:528:DyaK2cXhvFWjurs%3D

    Article  CAS  Google Scholar 

  • F Duus (1979) NoChapterTitle D Barton WD Ollis (Eds) Comprehensive organic chemistry NumberInSeries3 Pergamon New York 432

    Google Scholar 

  • HC Goldt AE Wanns (1961) J Org Chem 26 4047 Occurrence Handle10.1021/jo01068a097

    Article  Google Scholar 

  • Blackman LCF, Dewar MJS (1957) J Chem Soc:157

  • F Runge Z El-Hewchi HJ Renner E Taeger (1959) J Prakt Chem 7 279 Occurrence Handle10.1002/prac.19590070505 Occurrence Handle1:CAS:528:DyaF3cXhtFShsbw%3D

    Article  CAS  Google Scholar 

  • Z El-Hewchi (1962) J Prakt Chem 16 201 Occurrence Handle10.1002/prac.19620160314

    Article  Google Scholar 

  • GE McCasland AB Zanglungo LJ Durham (1976) J Org Chem 41 1125 Occurrence Handle10.1021/jo00869a008 Occurrence Handle1:CAS:528:DyaE28XhtlGqtL8%3D

    Article  CAS  Google Scholar 

  • Craighton AM, Owen LN (1960) J Chem Soc:1024

  • RL Frank SS Drake PV Smith C Stevens (1948) J Polymer Sci 2 50

    Google Scholar 

  • EE Reid (1958) Organic Chemistry of Bivalent Sulfur Chemical Publishing Company New York

    Google Scholar 

  • M Saeed M Abbas RJ Abdel-Jalil M Zahid W Voelter (2003) Tetrahedron Lett 44 315 Occurrence Handle10.1016/S0040-4039(02)02529-7 Occurrence Handle1:CAS:528:DC%2BD38XpsVems7o%3D

    Article  CAS  Google Scholar 

  • Leung MK, Hsieh DT, Lee KH, Liou JC (1995) J Chem Res:478

  • B Tamami AR Kiasat (1999) Iran Polym J 8 17 Occurrence Handle1:CAS:528:DyaK1MXjvV2gt78%3D

    CAS  Google Scholar 

  • FY Wang ZC Chen QG Zheng (2003) J Chem Res (S) 12 810 Occurrence Handle10.3184/030823403322840495

    Article  Google Scholar 

  • AWM Lee WH Chan HC Wong (1988) Synthetic Commun 18 1531 Occurrence Handle10.1080/00397918808081310 Occurrence Handle1:CAS:528:DyaL1MXnsVyjtA%3D%3D

    Article  CAS  Google Scholar 

  • A Sugawara M Shirahata S Sato R Sato (1984) Bull Chem Soc Jpn 57 3353 Occurrence Handle10.1246/bcsj.57.3353 Occurrence Handle1:CAS:528:DyaL2MXhtlWlt78%3D

    Article  CAS  Google Scholar 

  • A Sugawara K Husegawa KJ Suzuki Y Takahash R Saito (1987) Bull Chem Soc Jpn 60 435 Occurrence Handle10.1246/bcsj.60.435 Occurrence Handle1:CAS:528:DyaL2sXlslGnurk%3D

    Article  CAS  Google Scholar 

  • F Runge Z El-Hewechi HJ Renner E Taeger (1960) J Prakt Chem 11 284 Occurrence Handle10.1002/prac.19600110507 Occurrence Handle1:CAS:528:DyaF3MXjvVSiug%3D%3D

    Article  CAS  Google Scholar 

  • R Hurges C Hoock (1992) Angew Chem Int Ed 31 1611 Occurrence Handle10.1002/anie.199216111

    Article  Google Scholar 

  • Aoyagi N, Ochiai B, Mori H, Endo T (2006) Synlett:636

  • D Chaturvedi A Kumar S Ray (2002) Synth Commun 32 2651 Occurrence Handle10.1081/SCC-120006028 Occurrence Handle1:CAS:528:DC%2BD38XmslCrs7w%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi A Kumar S Ray (2003) Tetrahedron Lett 44 7637 Occurrence Handle10.1016/j.tetlet.2003.08.018 Occurrence Handle1:CAS:528:DC%2BD3sXnt1yitrc%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2005) Lett Org Chem 2 742 Occurrence Handle10.2174/157017805774717472 Occurrence Handle1:CAS:528:DC%2BD28XhsVOjtA%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2005) J Sulfur Chem 26 365 Occurrence Handle10.1080/17415990500404848 Occurrence Handle1:CAS:528:DC%2BD28XkvFynsw%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) J Sulfur Chem 27 265 Occurrence Handle10.1080/17415990600701697 Occurrence Handle1:CAS:528:DC%2BD28Xlt1Oit7Y%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Tetrahedron Lett 47 1307 Occurrence Handle10.1016/j.tetlet.2005.12.079 Occurrence Handle1:CAS:528:DC%2BD28XotFKiuw%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2006) Chinese Chem Lett 17 1309 Occurrence Handle1:CAS:528:DC%2BD28Xht1ahtrrF

    CAS  Google Scholar 

  • D Chaturvedi S Ray (2007) Tetrahedron Lett 48 149 Occurrence Handle10.1016/j.tetlet.2006.10.149 Occurrence Handle1:CAS:528:DC%2BD28Xht1yktrfF

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2007) J Sulfur Chem 28 39 Occurrence Handle10.1080/17415990601072262 Occurrence Handle1:CAS:528:DC%2BD2sXjs1amsLs%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2007) J Sulfur Chem 28 607 Occurrence Handle10.1080/17415990701670692 Occurrence Handle1:CAS:528:DC%2BD2sXht1aktLzJ

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2007) Tetrahedron Lett 48 5043 Occurrence Handle10.1016/j.tetlet.2007.05.103 Occurrence Handle1:CAS:528:DC%2BD2sXmvVKrsLY%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi N Mishra V Mishra (2008) Monatsh Chem 139 267 Occurrence Handle10.1007/s00706-007-0776-1 Occurrence Handle1:CAS:528:DC%2BD1cXitlamt7g%3D

    Article  CAS  Google Scholar 

  • Chaturvedi D, Mishra N, Mishra V (2008) Synthesis:355

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 201 Occurrence Handle10.1007/s00706-005-0417-5 Occurrence Handle1:CAS:528:DC%2BD28XotF2rsA%3D%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 311 Occurrence Handle10.1007/s00706-006-0438-8 Occurrence Handle1:CAS:528:DC%2BD28XitVCit70%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 459 Occurrence Handle10.1007/s00706-005-0452-2 Occurrence Handle1:CAS:528:DC%2BD28Xjt1KgtLs%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 465 Occurrence Handle10.1007/s00706-005-0460-2 Occurrence Handle1:CAS:528:DC%2BD28Xjt1Kgtbw%3D

    Article  CAS  Google Scholar 

  • D Chaturvedi S Ray (2006) Monatsh Chem 137 1219 Occurrence Handle10.1007/s00706-006-0514-0 Occurrence Handle1:CAS:528:DC%2BD28XptlOnsL4%3D

    Article  CAS  Google Scholar 

  • GW Kabalka M Varma RS Varma FF Knapp (1986) J Org Chem 51 2386 Occurrence Handle10.1021/jo00362a044 Occurrence Handle1:CAS:528:DyaL28XktVKht7c%3D

    Article  CAS  Google Scholar 

  • E Wertheim (1926) J Am Chem Soc 48 826 Occurrence Handle10.1021/ja01414a052 Occurrence Handle1:CAS:528:DyaB28XpslOl

    Article  CAS  Google Scholar 

  • Tamami B, Kiasat AR (1998) J Chem Res (S):454

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Devdutt Chaturvedi.

Additional information

Correspondence: Devdutt Chaturvedi, Bio-Organic Chemistry Division, Indian Institute of Integrative Medicine, Canal Road, Jammu-Tawi-18000, J&K, India.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chaturvedi, D., Mishra, N., Chaturvedi, A. et al. An efficient, one-pot synthesis of trithiocarbonates from alcoholic tosylates using the Cs2CO3/CS2 system. Monatsh Chem 139, 1467–1470 (2008). https://doi.org/10.1007/s00706-008-0956-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0956-7

Keywords

Navigation