Silica chloride in the presence of NaI is a useful system for the efficient and selective conversion of TMS, TBDMS and THP ethers into their corresponding iodides

被引:23
作者
Firouzabadi, H [1 ]
Iranpoor, N [1 ]
Hazarkhani, H [1 ]
机构
[1] Shiraz Univ, Dept Chem, Coll Sci, Shiraz 71454, Iran
关键词
D O I
10.1016/S0040-4039(02)01706-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct and highly selective conversion of benzylic, allylic and propargylic TMS, TBDMS and THP ethers into their corresponding iodides with the SiO2-Cl/NaI system is described. Reactions were conducted in CH3CN at room temperature. Aliphatic silyl and tetrahydropyranyl ethers remained almost intact under similar reaction conditions. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:7139 / 7141
页数:3
相关论文
共 32 条
[1]   REAGENTS AND SYNTHETIC METHODS .61. REACTION OF HINDERED TRIALKYSILYL ESTERS AND TRIALKYLSILYL ETHERS WITH TRIPHENYLPHOSPHINE DIBROMIDE - PREPARATION OF CARBOXYLIC-ACID BROMIDES AND ALKYL BROMIDES UNDER MILD NEUTRAL CONDITIONS [J].
AIZPURUA, JM ;
COSSIO, FP ;
PALOMO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4941-4943
[2]  
Ansell M. F., 1972, The Chemistry of Acyl Halides, P35
[3]  
Brown G. W., 1971, CHEM HYDROXYL GROU 1, P592
[4]   SULFURIC-ACID ADSORBED ON SILICA-GEL - A MULTIPURPOSE ACID CATALYST [J].
CHAVEZ, F ;
SUAREZ, S ;
DIAZ, MA .
SYNTHETIC COMMUNICATIONS, 1994, 24 (16) :2325-2339
[5]  
CORNELIS A, 1985, SYNTHESIS-STUTTGART, P909
[6]   Silica chloride (SiO2-Cl) promotes highly efficient transformation of acylals to dithianes, dithiolanesm, and oxathiolanes [J].
Firouzabadi, H ;
Iranpoor, N ;
Hazarkhani, H .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2001, 176 :165-171
[7]   Reactions of silica chloride (SiO2Cl)/DMSO, a heterogeneous system for the facile regeneration of carbonyl compounds from thioacetals and ring-expansion annelation of cyclic thioacetals [J].
Firouzabadi, H ;
Iranpoor, N ;
Hazarkhani, H ;
Karimi, B .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2572-2576
[8]  
Firouzabadi H, 2000, SYNLETT, P263
[9]  
FIROUZABADI H, IN PRESS SYNTH COMMU
[10]  
Greene T.W., 1991, PROTECTIVE GROUPS OR, V2nd