Highly regioselective ring-opening of epoxides with thiophenols in ionic liquids without the use of any catalyst

被引：78

作者：

Chen, JX

Wu, HY

Jin, C

Zhang, XX

Xie, YY

Su, WK ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 325027, Peoples R China

[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Zhejiang Key Lab Pharmaceut Engn, Hangzhou 310014, Peoples R China

来源：

GREEN CHEMISTRY | 2006年 / 8卷 / 04期

关键词：

D O I：

10.1039/b600620e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Clean thiolysis reaction of various epoxides in ionic liquids (ILs) without the use of any catalyst generates beta-hydroxy sulfides in excellent yields ( 83 - 98%) with high regioselectivity and chemoselectivity under mild reaction conditions.

引用

页码：330 / 332

页数：3

共 48 条

[1]

ALBANESE D, 1994, SYNTHESIS-STUTTGART, P34

[2] ZnCl2 as an efficient catalyst in the thiolysis of 1,2-epoxides by thiophenol in aqueous medium [J].

Amantini, D ;

Fringuelli, F ;

Pizzo, F ;

Tortoioli, S ;

Vaccaro, L .

SYNLETT, 2003, (15) :2292-2296

[3] Polymer-supported indium Lewis acid: Highly versatile catalyst for regio- and stereoselective ring-opening of epoxides [J].

Bandini, M ;

Fagioli, M ;

Melloni, A ;

Umani-Ronchi, A .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (05) :573-578

[4] Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to β-hydroxyamines [J].

Bolli, MH ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2243-2246

[5] REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES [J].

BONINI, C ;

RIGHI, G .

SYNTHESIS-STUTTGART, 1994, (03) :225-238

[6] Homogeneous biocatalysis in organic solvents and water-organic mixtures [J].

Castro, GR ;

Knubovets, T .

CRITICAL REVIEWS IN BIOTECHNOLOGY, 2003, 23 (03) :195-231

[7] Highly efficient cleavage of epoxides catalyzed by B(C6F5)3 [J].

Chandrasekhar, S ;

Reddy, CR ;

Babu, BN ;

Chandrashekar, G .

TETRAHEDRON LETTERS, 2002, 43 (21) :3801-3803

[8] Efficient synthesis of (R)- and (S)-3-octanol, (R)-2-dodecanol, (R)-2-methyl-4-heptanol and (R)-2-methyl-4-octanol:: the pheromones of Myrmica scabrinodis, Crematogaster castanea, C-liengmei, C-auberti and Metamasius hemipterus [J].

Cho, BT ;

Kim, DJ .

TETRAHEDRON, 2003, 59 (14) :2457-2462

[9]

CHOI J, 1995, SYNTHESIS-STUTTGART, P373

[10] 3,4-EPOXYPRECOCENES AS MODELS OF CYTOTOXIC EPOXIDES - SYNTHESIS OF THE CIS ADDUCTS OCCURRING IN THE GLUTATHIONE METABOLIC PATHWAY [J].

CONCHILLO, A ;

CAMPS, F ;

MESSEGUER, A .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1728-1735

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