Bismuth compounds in organic synthesis. Deprotection of ketoximes using bismuth bromide-bismuth triflate

被引:26
作者
Arnold, JN [1 ]
Hayes, PD [1 ]
Kohaus, RL [1 ]
Mohan, RS [1 ]
机构
[1] Illinois Wesleyan Univ, Dept Chem, Lab Environm Friendly Organ Synth, Bloomington, IL 61701 USA
关键词
bismuth and compounds; oximes; deprotection; environment-friendly chemistry;
D O I
10.1016/j.tetlet.2003.10.031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ketoximes undergo deprotection in CH3CN/acetone/H2O (3:6:1) in the presence of 20-40 mol% BiBr3/5 mol% Bi(OTf)(3). Bismuth(III) salts are relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively non-toxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9173 / 9175
页数:3
相关论文
共 24 条
[1]  
[Anonymous], AM CHEM SOC S SERIES
[2]  
[Anonymous], CHEM ARSENIC ANTIMON
[3]  
[Anonymous], 1999, PROTECTING GROUPS OR
[4]   Facile regeneration of carbonyl compounds from oximes and tosylhydrazones with TBHP [J].
Barhate, NB ;
Gajare, AS ;
Wakharkar, RD ;
Sudalai, A .
TETRAHEDRON LETTERS, 1997, 38 (04) :653-656
[5]   Regeneration of carbonyl compounds from oximes under microwave irradiations [J].
Boruah, A ;
Baruah, B ;
Prajapati, D ;
Sandhu, JS .
TETRAHEDRON LETTERS, 1997, 38 (24) :4267-4268
[6]   A facile method for the conversion of oximes and tosylhydrazones to carbonyl compounds with Dess-Martin periodinane [J].
Bose, DS ;
Narsaiah, AV .
SYNTHETIC COMMUNICATIONS, 1999, 29 (06) :937-941
[7]  
Brezinski B., 1991, J CHEM SOC P2, V2, P857
[8]   Manganese triacetate mediated regeneration of carbonyl compounds from oximes [J].
Demir, AS ;
Tanyeli, C ;
Altinel, E .
TETRAHEDRON LETTERS, 1997, 38 (41) :7267-7270
[9]  
Greene T. W., 1999, PROTECTIVE GROUPS OR
[10]   Microwave assisted conversion of oximes and semicarbazones to carbonyl compounds using benzyltriphenylphosphonium peroxymonosulfate [J].
Hajipour, AR ;
Mallakpour, SE ;
Mohammadpoor-Baltork, I ;
Adibi, H .
MONATSHEFTE FUR CHEMIE, 2003, 134 (01) :45-49