Studies on novel synthetic methodologiess Part 39. Simple, mild and efficient thioacetalization and transthioacetalization of carbonyl compounds and deprotection of thioacetals: Unique role of thiols in the selectivity of thioacetalization

被引:44
作者
Das, B [1 ]
Ramu, R [1 ]
Reddy, MR [1 ]
Mahender, G [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2005年 / 02期
关键词
carbonyl compounds; thioacetalization; transthioacetalization; deprotection of thioacetals; NaHSO4 center dot SiO2; selectivity;
D O I
10.1055/s-2004-834934
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Silica supported sodium hydrogen sulfate (NaHSO4.SiO2) has been employed for efficient thioacetalization and transthioacetalization of carbonyl compounds in CH(2)C(l)2 at room temperature. Selectivity of thioacetalization was dependent on the thiols used for the conversion. The same catalyst was also found to be effective for deprotection of thioacetals in CH2Cl2-H2O at room temperature.
引用
收藏
页码:250 / 254
页数:5
相关论文
共 25 条
[2]   TOTAL SYNTHESIS OF (+-)-TRICHODERMIN [J].
COLVIN, EW ;
RAPHAEL, RA ;
ROBERTS, JA .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (15) :858-&
[3]   PHENYLTHIOMETHYLLITHIUM AND BIS(PHENYLTHIO)METHYLLITHIUM [J].
COREY, EJ ;
SEEBACH, D .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4097-&
[4]   OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].
COREY, EJ ;
ERICKSON, BW .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&
[5]   CARBANIONS OF 1,3-DITHIANES . REAGENTS FOR C-C BOND FORMATION BY NUCLEOPHILIC DISPLACEMENT AND CARBONYL ADDITION [J].
COREY, EJ ;
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1965, 4 (12) :1075-&
[6]   MAGNESIUM AND ZINC-CATALYZED THIOKETALIZATION [J].
COREY, EJ ;
SHIMOJI, K .
TETRAHEDRON LETTERS, 1983, 24 (02) :169-172
[7]  
DISHI T, 1972, TETRAHEDRON LETT, V13, P1085
[8]   STUDIES IN ORGANIC SULFUR COMPOUNDS .6. CYCLIC ETHYLENE AND TRIMETHYLENE HEMITHIOKETALS [J].
DJERASSI, C ;
GORMAN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3704-3708
[9]  
ELLISON RA, 1975, TETRAHEDRON LETT, P499
[10]   PREPARATION OF ETHYLENETHIOKETALS [J].
FIESER, LF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (07) :1945-1947