Skip to main content
SpringerLink
Log in

The rapid and efficient synthesis of disulfides from alkyl and acyl halides

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

Abstract

Various symmetrical dialkyl and diacyl disulfides are prepared easily in high yields from the corresponding alkyl and acyl halides under mild and nonaqueous conditions using N,N′-dibutyl-N,N,N′,N′-tetramethyl-ethylenediammonium tetrahydroborate (BTMETB) or N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium tetrahydroborate (BZTMETB) and elemental sulfur. The quaternary diammonium borohydrides were easily prepared by treatment of the corresponding quaternary diammonium chloride or bromide with alkaline solution of sodium borohydride at room temperature.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • S Oae (Eds) (1991) Organic Sulfur Chemistry: Structure and Mechanism CRC Boca Raton, FL

    Google Scholar 

  • DC Jocelyn (1992) Biochemistry of the Thiol Groups Academic New York

    Google Scholar 

  • RJ Cremlyn (1996) An Introduction to Organosulfur Chemistry Wiley & Sons New York

    Google Scholar 

  • S Oae (1977) Organic Chemistry of Sulfur Plenum Press New York

    Google Scholar 

  • Olah GA, Arvanaghi M, Vankar YD (1979) Synthesis:721

  • Drabowica J, Mikotaczyk M (1980) Synthesis:32

  • H Firouzabadi N Iranpoor H Parhan A Sardarian J Toofan (1984) Synth Commun 14 717 Occurrence Handle10.1080/00397918408059586 Occurrence Handle1:CAS:528:DyaL2cXlslShsrs%3D

    Article  CAS  Google Scholar 

  • JP Mahieu M Gosselet B Sebill Y Beuzard (1986) Synth Commun 16 1709 Occurrence Handle10.1080/00397918608056430 Occurrence Handle1:CAS:528:DyaL1cXls1Sntw%3D%3D

    Article  CAS  Google Scholar 

  • KA Pemriashvili VA Usov MF Larik MG Voronkov (1986) Zh Org Khim XXII 454

    Google Scholar 

  • Firouzabadi H, Mottghinejad E, Seddighi M (1989) Synthesis:378

  • T Sato J Otera H Nozaki (1990) Tetrahedron Lett 31 3591 Occurrence Handle10.1016/S0040-4039(00)94450-2 Occurrence Handle1:CAS:528:DyaK3cXlvFSnt7w%3D

    Article  CAS  Google Scholar 

  • DHR Barton C Chen GM Wall (1991) Tetrahedron 47 6127 Occurrence Handle10.1016/S0040-4020(01)86546-7 Occurrence Handle1:CAS:528:DyaK3MXmtVOrsLo%3D

    Article  CAS  Google Scholar 

  • S Akabori Y Takanohashi S Takagi (1990) Synth Commun 20 3187 Occurrence Handle10.1080/00397919008051544 Occurrence Handle1:CAS:528:DyaK3MXot1SqsQ%3D%3D

    Article  CAS  Google Scholar 

  • A Mckillop D Koyuncu (1990) Tetrahedron Lett 31 5007 Occurrence Handle10.1016/S0040-4039(00)97790-6 Occurrence Handle1:CAS:528:DyaK3MXmtFKgsw%3D%3D

    Article  CAS  Google Scholar 

  • H Fujihara H Mima M Ikemori N Furukawa (1991) J Am Chem Soc 113 6337 Occurrence Handle10.1021/ja00016a097 Occurrence Handle1:CAS:528:DyaK3MXkvFaitb4%3D

    Article  CAS  Google Scholar 

  • H Suzuki S Kawato A Nasu (1992) Bull Chem Soc Jpn 62 626 Occurrence Handle10.1246/bcsj.65.626

    Article  Google Scholar 

  • BO Broin R Darcy (1993) Synth Commun 23 1209 Occurrence Handle10.1080/00397919308011205 Occurrence Handle1:CAS:528:DyaK3sXlsF2kurk%3D

    Article  CAS  Google Scholar 

  • B Movassagh MM Lakouraj K Ghodreti (1999) Synth Commun 29 3597 Occurrence Handle10.1080/00397919908085994 Occurrence Handle1:CAS:528:DyaK1MXltlakt7g%3D

    Article  CAS  Google Scholar 

  • M Tajbakhsh I Mohammadpoor-baltork K Alimohammadi (2003) Monatsh Chem 134 1571 Occurrence Handle1:CAS:528:DC%2BD3sXps1Gqurs%3D

    CAS  Google Scholar 

  • RL Frank JR Blegen (1995) Org Synth Coll 3 116

    Google Scholar 

  • SV Amosova VV Nosyreva MV Sigalov (1992) Zh Org Khim 28 927 Occurrence Handle1:CAS:528:DyaK3sXhtVWnurc%3D

    CAS  Google Scholar 

  • YO Gabel LF Shpeier (1947) J Gen Chem USSR 17 2277 Occurrence Handle1:CAS:528:DyaH1cXitlWquw%3D%3D

    CAS  Google Scholar 

  • GC Chokravarit (1928) J Indian Chem Soc 5 405

    Google Scholar 

  • V Polshettiwar M Nivsarkar J Acharya MP Kaushik (2003) Tetrahedron Lett 44 887 Occurrence Handle10.1016/S0040-4039(02)02776-4 Occurrence Handle1:CAS:528:DC%2BD3sXhtFCntrc%3D

    Article  CAS  Google Scholar 

  • JX Wang W Cui Y Hu K Zhao (1995) Synth Commun 25 889 Occurrence Handle10.1080/00397919508013426 Occurrence Handle1:CAS:528:DyaK2MXjslChu7o%3D

    Article  CAS  Google Scholar 

  • JX Wang W Cui Y Hu (1995) Synth Commun 25 3573 Occurrence Handle10.1080/00397919508015492 Occurrence Handle1:CAS:528:DyaK2MXot1OlsL0%3D

    Article  CAS  Google Scholar 

  • JX Wang L Gao D Huang (2002) Synth Commun 32 963 Occurrence Handle10.1081/SCC-120003143 Occurrence Handle1:CAS:528:DC%2BD38XjvV2ltL4%3D

    Article  CAS  Google Scholar 

  • A Ogawa N Takami M Sekiguchi N Sonoda T Hirao (1998) Heteroatom Chem 9 581 Occurrence Handle10.1002/(SICI)1098-1071(1998)9:6<581::AID-HC9>3.0.CO;2-7 Occurrence Handle1:CAS:528:DyaK1cXmsVyhtbc%3D

    Article  CAS  Google Scholar 

  • Jia XS, Liu XT, Li Q, Huang Q, Kong LL (2006) J Chem Res:547

  • B Tamami AR Kiasat (1998) Synth Commun 28 1275 Occurrence Handle10.1080/00397919808005969 Occurrence Handle1:CAS:528:DyaK1cXitleltr0%3D

    Article  CAS  Google Scholar 

  • BP Bandgar LS Uppalla VS Sadavarte (2001) Tetrahedron Lett 42 6741 Occurrence Handle10.1016/S0040-4039(01)00789-4 Occurrence Handle1:CAS:528:DC%2BD3MXmt1yqtL8%3D

    Article  CAS  Google Scholar 

  • RG Hiskey BD Thomas JA Kepler (1964) J Org Chem 29 3671 Occurrence Handle10.1021/jo01035a060 Occurrence Handle1:CAS:528:DyaF2MXhsFWktg%3D%3D

    Article  CAS  Google Scholar 

  • SA Okecha (1980) Chem Ind (London, United Kingdom) 19 788

    Google Scholar 

  • AK Misra G Agnihotri (2004) Synth Comm 34 1079 Occurrence Handle10.1081/SCC-120028640 Occurrence Handle1:CAS:528:DC%2BD2cXitVamtrk%3D

    Article  CAS  Google Scholar 

  • R Leino JE Lonnqvist (2004) Tetrahedron Lett 45 8489 Occurrence Handle10.1016/j.tetlet.2004.09.100 Occurrence Handle1:CAS:528:DC%2BD2cXos1aqu7g%3D

    Article  CAS  Google Scholar 

  • DA Lattle EH Jensen WA Struck (1952) Anal Chem 24 1843 Occurrence Handle10.1021/ac60071a041

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Mazandaran University, Babolsar, Iran

    Mahmood Tajbakhsh, Moslem M. Lakouraj & Majid S. Mahalli

Authors
  1. Mahmood Tajbakhsh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Moslem M. Lakouraj
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Majid S. Mahalli
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mahmood Tajbakhsh.

Additional information

Correspondence: Mahmood Tajbakhsh, Department of Chemistry, Mazandaran University, Babolsar, Iran.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tajbakhsh, M., Lakouraj, M. & Mahalli, M. The rapid and efficient synthesis of disulfides from alkyl and acyl halides. Monatsh Chem 139, 1453–1456 (2008). https://doi.org/10.1007/s00706-008-0950-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-008-0950-0

Keywords

Search

Navigation