3,5-dimethylpyrazolium fluorochromate(VI), C5H8N2H[CrO3F], (DmpzHFC):: a convenient new reagent for oxidation of organic substrates

被引:57
作者
Bora, U
Chaudhuri, MK [1 ]
Dey, D
Kalita, D
Kharmawphlang, W
Mandal, GC
机构
[1] Indian Inst Technol, Dept Chem, Guwahati 781031, India
[2] NE Hill Univ, Dept Chem, Shillong 793022, Meghalaya, India
关键词
alcohols; polycyclic hydrocarbons; Delta(5)-steroids; chromium(VI); oxidations;
D O I
10.1016/S0040-4020(01)00116-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new chromium(VI) reagent, 3,5-dimethylpyrazolium fluorochromate, C5H8N2H[CrO3F] (DmpzHFC), has been developed by reacting dmpz with CrO3 and aqueous HF for the selective oxidation of primary, secondary and allylic alcohols to the corresponding carbonyl compounds, polycyclic hydrocarbons to cyclic ketones and allylic Delta (5) steroids to the corresponding alpha,beta -unsaturated ketones. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2445 / 2448
页数:4
相关论文
共 35 条
[1]   KINETICS AND MECHANISM OF THE OXIDATION OF AROMATIC-ALDEHYDES BY PYRIDINIUM FLUOROCHROMATE [J].
AGARWAL, S ;
CHOWDHURY, K ;
BANERJI, KK .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5111-5113
[2]  
AKHREM AA, 1970, TOTAL STEROID SYNTHE
[4]   OXIDATION OF ALIPHATIC-ALCOHOLS BY PYRIDINIUM FLUOROCHROMATE - A KINETIC-STUDY [J].
BANERJI, KK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (04) :547-549
[5]   A SHORT TOTAL SYNTHESIS OF ESTRONE DERIVATIVES - A NOVEL 1,3-REARRANGEMENT OF AN ALLYLIC NITRO-GROUP [J].
BARLAAM, B ;
BOIVIN, J ;
ELKAIM, L ;
ELTONFARR, S ;
ZARD, SZ .
TETRAHEDRON, 1995, 51 (06) :1675-1684
[6]   PYRIDINIUM FLUOROCHROMATE - A NEW AND EFFICIENT OXIDANT FOR ORGANIC SUBSTRATES [J].
BHATTACHARJEE, MN ;
CHAUDHURI, MK ;
DASGUPTA, HS ;
ROY, N ;
KHATHING, DT .
SYNTHESIS-STUTTGART, 1982, (07) :588-590
[7]   SOME ASPECTS OF PYRIDINIUM FLUOROCHROMATE, C5H5NHCRO3F(PFC), OXIDATIONS - STOICHIOMETRY OF OXIDATION OF ALCOHOLS, EVIDENCE FOR OXYGEN-TRANSFER, AND THE IDENTITY OF THE REDUCED CHROMIUM SPECIES [J].
BHATTACHARJEE, MN ;
CHAUDHURI, MK ;
PURKAYASTHA, S .
TETRAHEDRON, 1987, 43 (22) :5389-5392
[8]  
BHATTACHARJEE MN, 1990, INORG SYNTH, V27, P310
[9]   Regioselective bromination of organic substrates by tetrabutylammonium bromide promoted by V2O5-H2O2:: An environmentally favorable synthetic protocol [J].
Bora, U ;
Bose, G ;
Chaudhuri, MK ;
Dhar, SS ;
Gopinath, R ;
Khan, AT ;
Patel, BK .
ORGANIC LETTERS, 2000, 2 (03) :247-249
[10]   QUINOLINIUM FLUOROCHROMATE (QFC), C9H7NH[CRO3F] - AN IMPROVED CR(VI)-OXIDANT FOR ORGANIC SUBSTRATES [J].
CHAUDHURI, MK ;
CHETTRI, SK ;
LYNDEM, S ;
PAUL, PC ;
SRINIVAS, P .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (07) :1894-1898