Summary.
Ethylenebis(N-methylimidazolium) chlorochromate was prepared by addition of N-methylimidazole to 1,2-dibromoethane to form the corresponding dibromide salt and subsequent treatment of this salt with CrO3 in 6N HCl solution. It is a stable yellow-orange solid, which oxidized thiols to the corresponding disulfides at room temperature. Selective oxidation of thiols in the presence of sulfides and hydroxyl groups was also achieved with this reagent.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M Bodanszky (1984) Principles of Peptide Synthesis Springer Berlin
JR Johnson WF Bruce JD Dutcher (1943) J Am Chem Soc 65 2005 Occurrence Handle10.1021/ja01250a051 Occurrence Handle1:CAS:528:DyaH2cXmvFQ%3D
a) Liu KT, Tong YC (1978) Synthesis 669; b) Wallace TJ (1996) J Org Chem 31: 3071; c) Sato T, Otera J, Nozaki H (1990) Tetrahederon Lett 31: 3591; d) Pryor WA, Church DF, Govindan CK, Crank G (1982) J Org Chem 47: 156; e) Schaeffer JR, Goodhue CD, Risle HA, Stevens RE (1967) J Org Chem 32: 392; f) Drabowicz J, Mikolajczyk M (1980) Synthesis 32; g) Ali MH, McDermott M (2002) Tetrahedron Lett 43: 6271; h) Aida T, Akasaka T, Furukawa N, Oae S (1976) Bull Chem Soc Jpn 49: 1441; i) McKillop A, Koyuncu D (1990) Tetrahedron Lett 31: 5007; j) Choi J, Yoon NM (1995) J Org Chem 60: 3266; k) Ramadas K, Srinivasan N (1996) Synth Commun 26: 4179; l) Salehi P, Farrokhi A, Gholizadeh M (2001) Synth Commun 31: 2777; m) Tajbakhsh M, Hosseinzadeh R, Shakoori A (2004) „Tetrahedron Lett 45: 1889; n) Varma RS, Meshram HM, Dahiya R (2000) Synth Commun 30: 1249; o) Noureldin NA, Caldwell M, Hendry J, Lee DG (1998) Synthesis 1587; p) Evans BJ, Doi JT, Musker WK (1990) J Org Chem 55: 2337; q) Shaabani A, Lee DG (2001) Tetrahedron Lett 42: 5833; r) Iranpoor N, Firouzabadi H, Paurali AR (2002) Tetrahedron 58: 5179; s) Shah AST, Khan MK, Fecker M, Volter W (2003) Tetrahedron Lett 44: 6789
a) Hosseinzadeh R, Tajbakhsh M, Niaki MY (2002) Tetrahedron Lett 43: 9413; b) Tajbakhsh M, Hosseinzadeh R, Sadatshahabi M (2005) Synth Commun 35: 1547; c) Hosseinzadeh R, Tajbakhsh M, Vahedi H (2005) Synlett 2769
M Tajbakhsh M Ghaemi S Sarabi M Ghasemzadeh MM Heravi (2000) Monatsh Chem 131 1213 Occurrence Handle1:CAS:528:DC%2BD3MXhtFejuw%3D%3D
a) Field L, Lawson JE (1958) J Am Chem Soc 80: 838; b) Wallace TJ (1964) J Am Chem Soc 86: 2018; c) Yiannios CN, Karabinos JV (1963) J Org Chem 28: 3246; d) Raghavan S, Rajender A, Joseph SC, Rasheed MA (2001) Synth Commun 31: 1477; e) Champman H (1982) Dictionary of Organic Compounds, 5th edn, Vol. II. New York, p 2376; f) Harrison, DC (1927) Biochem J 21: 1404; g) Sanz R, Aguado R, Pedrosa MR, Arnaiz FJ (2002) Synthesis 856; h) Meshram HM, Bandyopdhyay A, Reddy GS, Yadav JS (2000) Synth Commun 30: 701; i) Khazaei A, Zolfigol MA, Rostami A (2004) Synthesis 2959; j) Firouzabadi H, Mohadjer D, Entezari-Moghadam M (1988) Bull Chem Soc Jpn 31: 1217
B Movassagh MM Lakouraj K Ghodrati (1999) Synth Commun 29 3597 Occurrence Handle1:CAS:528:DyaK1MXltlakt7g%3D
B Movassagh MM Lakouraj K Ghodrati (2002) Indian J Chem 41B 1293 Occurrence Handle1:CAS:528:DC%2BD38XkvVektLo%3D
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hosseinzadeh, R., Tajbakhsh, M., Khaledi, H. et al. Ethylenebis(N-methylimidazolium) Chlorochromate (EBMICC): An Efficient and Selective Reagent for the Oxidation of Thiols to Disulfides. Monatsh. Chem. 138, 871–873 (2007). https://doi.org/10.1007/s00706-007-0685-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-007-0685-3