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Mild and Efficient Ring Opening of Epoxides Catalyzed by Potassium Dodecatungstocobaltate(III)

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Summary.

Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst.

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References

  • Bonini C, Righi G (1994) Synthesis 225

  • N Iranpoor I Mohammadpoor-Baltork (1990) Synth Commun 20 2789 Occurrence Handle1:CAS:528:DyaK3MXht1Sqtbg%3D

    CAS  Google Scholar 

  • Shimizu M, Yoshida A, Fujisava T (1992) Synlett 204

  • S Munavalli DK Rohrbaugh FJ Berg FR Longo HD Durst (2002) Phosp Sulfur Silicon 177 215 Occurrence Handle1:CAS:528:DC%2BD38Xmt1eltr0%3D

    CAS  Google Scholar 

  • AS Rao SK Paknikar JG Kirtune (1983) Tetrahedron 39 2323 Occurrence Handle10.1016/S0040-4020(01)91961-1 Occurrence Handle1:CAS:528:DyaL3sXlsFyitro%3D

    Article  CAS  Google Scholar 

  • Olah GA, Fung AP, Mieder D (1981) Synthesis 280

  • GH Posner DZ Rogers CH Kinzig GM Gurria (1975) Tetrahedron Lett 16 3597

    Google Scholar 

  • J Otera Y Yoshida K Hirakawa (1985) Tetrahedron Lett 26 3219 Occurrence Handle10.1016/S0040-4039(00)98156-5 Occurrence Handle1:CAS:528:DyaL28XmvVaqsg%3D%3D

    Article  CAS  Google Scholar 

  • GH Posner DZ Rogers (1977) J Am Chem Soc 99 8208 Occurrence Handle1:CAS:528:DyaE1cXms1an

    CAS  Google Scholar 

  • GH Posner DZ Rogers (1977) J Am Chem Soc 99 8214 Occurrence Handle1:CAS:528:DyaE1cXms1am

    CAS  Google Scholar 

  • M Chini P Crotti L Favero M Pineschi (1994) Tetrahedron Lett 35 433 Occurrence Handle1:CAS:528:DyaK2cXktVylsLc%3D

    CAS  Google Scholar 

  • N Iranpoor I Mohammadpoor-Baltork (1990) Tetrahedron Lett 31 735 Occurrence Handle10.1016/S0040-4039(00)94616-1 Occurrence Handle1:CAS:528:DyaK3cXksVSjtrw%3D

    Article  CAS  Google Scholar 

  • N Iranpoor I Mohammadpoor-Baltork F Shiriny Zardaloo (1991) Tetrahedron 47 9861 Occurrence Handle1:CAS:528:DyaK38XotlCltg%3D%3D

    CAS  Google Scholar 

  • BM Cheudary Y Sudha (1996) Synth Commun 26 2989

    Google Scholar 

  • Iranpoor N, Salehi P (1994) Synthesis 1152

  • Masaki Y, Miura T, Ochiai M (1993) Synlett 847

  • Y Masaki T Miura M Ochiai (1996) Bull Chem Soc Jpn 69 195 Occurrence Handle1:CAS:528:DyaK28XlslahsQ%3D%3D

    CAS  Google Scholar 

  • Iranpoor N, Tarrian T, Movahedi Z (1996) Synthesis 1473

  • EN Jacobsen F Kakiuchi RG Konsler JF Larrow M Tokunaga (1997) Tetrahedron Lett 38 773 Occurrence Handle10.1016/S0040-4039(96)02414-8 Occurrence Handle1:CAS:528:DyaK2sXhtVKgtbw%3D

    Article  CAS  Google Scholar 

  • Y Taniguch S Tanaka T Kitamura Y Fujiwara (1998) Tetrahedron Lett 39 4559

    Google Scholar 

  • N Iranpoor M Shekarriz F Shiriny (1998) Synth Commun 28 347 Occurrence Handle1:CAS:528:DyaK1cXhtlaru7k%3D

    CAS  Google Scholar 

  • I Mohammadpoor-Baltork S Tangestaninejad H Aliyan V Mirkhani (2000) Synth Commun 30 2365 Occurrence Handle1:CAS:528:DC%2BD3cXjslyqs7Y%3D

    CAS  Google Scholar 

  • H Sharghi M Nasseri Ali K Niknam (2001) J Org Chem 66 7287 Occurrence Handle10.1021/jo0103266 Occurrence Handle1:CAS:528:DC%2BD3MXntlGqsrc%3D

    Article  CAS  Google Scholar 

  • DL Fox AA Robinson JB Frank RN Salvatore (2003) Tetrahedron Lett 44 7579 Occurrence Handle1:CAS:528:DC%2BD3sXnt1yisbg%3D

    CAS  Google Scholar 

  • T Ollevier G Lavie-Compin (2002) Tetrahedron Lett 43 7891 Occurrence Handle10.1016/S0040-4039(02)01896-8 Occurrence Handle1:CAS:528:DC%2BD38Xns12jtLY%3D

    Article  CAS  Google Scholar 

  • S Tangestaninejad V Mirkhani (1999) Synth Commun 29 2079 Occurrence Handle1:CAS:528:DyaK1MXivVOjtrs%3D

    CAS  Google Scholar 

  • Tangestaninejad S, Habibi MH, Mirkhani V, Moghadam M (2001) J Chem Res (S) 365

  • Tangestaninejad S, Mirkhani V (1999) J Chem Res (S) 370

  • M Moghadam S Tangestaninejad V Mirkhani R Shaibani (2004) Tetrahedron 60 6105 Occurrence Handle10.1016/j.tet.2004.05.069 Occurrence Handle1:CAS:528:DC%2BD2cXlt1ekurc%3D

    Article  CAS  Google Scholar 

  • T Okuhara N Mizuno M Misono (1996) Adv Catal 41 113 Occurrence Handle1:CAS:528:DyaK28XltFyjtb4%3D

    CAS  Google Scholar 

  • Izumi Y, Urabe K, Onaka A (1992) Zeolite, Clay and Heteropoly Acid in Organic Reaction; VCH/Weinheim: Kodansha/Tokyo

  • Izumi Y, Hayashi K (1980) Chem Lett 787

  • Y Izumi K Hayashi (1982) J Mol Catal 18 299

    Google Scholar 

  • E Rafiee S Tangestaninejad MH Habibi V Mirkhani (2004) Bioorg & Med Chem Lett 14 3611 Occurrence Handle1:CAS:528:DC%2BD2cXks1GmsLo%3D Occurrence Handle10.1016/j.bmcl.2004.03.110

    Article  CAS  Google Scholar 

  • MH Habibi S Tangestaninejad V Mirkhani B Yadollahi (2001) Tetrahedron 57 8333 Occurrence Handle10.1016/S0040-4020(01)00806-7 Occurrence Handle1:CAS:528:DC%2BD3MXmvFCjurY%3D

    Article  CAS  Google Scholar 

  • MH Habibi S Tangestaninejad I Mohammadpoor-Baltork V Mirkhani B Yadollahi (2001) Tetrahedron Lett 42 6771 Occurrence Handle1:CAS:528:DC%2BD3MXmt1yqtLY%3D

    CAS  Google Scholar 

  • MH Habibi S Tangestaninejad I Mohammadpoor-Baltork V Mirkhani B Yadollahi (2001) Tetrahedron Lett 42 2851 Occurrence Handle1:CAS:528:DC%2BD3MXisVKht7k%3D

    CAS  Google Scholar 

  • MH Habibi S Tangestaninejad V Mirkhani B Yadollahi (2001) Catalysis Lett 75 205 Occurrence Handle1:CAS:528:DC%2BD3MXotFOrsb8%3D

    CAS  Google Scholar 

  • V Mirkani S Tangestaninejad B Yadollahi L Alipanah (2003) Tetrahedron 59 8213

    Google Scholar 

  • V Mirkani S Tangestaninejad L Alipanah (2002) Synth Commun 32 621

    Google Scholar 

  • V Mirkani S Tangestaninejad B Yadollahi L Alipanah (2003) Catalysis Lett 91 129

    Google Scholar 

  • M Sunder (1996) Chem Rev 66 297

    Google Scholar 

  • E Vedejs GA Kraffi (1982) Tetrahedron 38 2857 Occurrence Handle10.1016/0040-4020(82)85013-8 Occurrence Handle1:CAS:528:DyaL3sXhsl2isrs%3D

    Article  CAS  Google Scholar 

  • Jankowski K, Harry R (1972) Synthesis 627

  • H Bouda ME Borredon M Delmas A Gaset (1989) Synth Commun 19 491 Occurrence Handle1:CAS:528:DyaK3cXlsFCkug%3D%3D

    CAS  Google Scholar 

  • R Ketcham VP Shah (1963) J Org Chem 28 229 Occurrence Handle1:CAS:528:DyaF3sXlvFKjuw%3D%3D

    CAS  Google Scholar 

  • FG Bordwell MH Anderson (1953) J Am Chem Soc 75 4959 Occurrence Handle1:CAS:528:DyaG2cXnslCkuw%3D%3D

    CAS  Google Scholar 

  • TH Chan JR Finkenbine (1972) J Am Chem Soc 94 2880 Occurrence Handle10.1021/ja00763a068 Occurrence Handle1:CAS:528:DyaE38XhsFejsrY%3D

    Article  CAS  Google Scholar 

  • I Mohammadpoor-Baltork AR Khosropour (1999) Indian J Chem 38 605

    Google Scholar 

  • N Iranpoor B Zaynizadeh (1998) Synth Commun 28 3913 Occurrence Handle1:CAS:528:DyaK1cXmsl2lur4%3D

    CAS  Google Scholar 

  • B Tamami AR Kiasat (1996) Synth Commun 26 3953 Occurrence Handle1:CAS:528:DyaK28XmtFWrsr8%3D

    CAS  Google Scholar 

  • Iranpoor N, Kazemi F (1996) Synthesis 821

  • N Iranpoor F Kazemi (1997) Tetrahedron 53 11377 Occurrence Handle10.1016/S0040-4020(97)00719-9 Occurrence Handle1:CAS:528:DyaK2sXls1Ggsb8%3D

    Article  CAS  Google Scholar 

  • S Funabashi (1995) J Org Chem 60 3953

    Google Scholar 

  • J Sara C Robert A Geoffry (1992) Aust J Chem 45 1943

    Google Scholar 

  • J Sara C Robert T Hambley (1992) Aust J Chem 45 685

    Google Scholar 

  • T Pope M Gideon (1960) Inorg Chem 7 1249

    Google Scholar 

  • C Sanchez J Livage M Fournier (1984) Inorg Chem 23 17

    Google Scholar 

  • LCW Baker TD Mc Cutcheon (1956) J Am Chem Soc 78 4503 Occurrence Handle1:CAS:528:DyaG2sXisVOntg%3D%3D

    CAS  Google Scholar 

  • Eberson L, Wistrand LG (1980) Acta Chem Scand Ser B 34

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Correspondence to Shahram Tangestaninejad.

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Tangestaninejad, S., Moghadam, M., Mirkhani, V. et al. Mild and Efficient Ring Opening of Epoxides Catalyzed by Potassium Dodecatungstocobaltate(III). Monatsh. Chem. 137, 235–242 (2006). https://doi.org/10.1007/s00706-005-0415-7

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  • DOI: https://doi.org/10.1007/s00706-005-0415-7

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