Easy and environmentally friendly uncatalyzed synthesis of β-hydroxy arylsulfides by thiolysis of 1,2-epoxides in water

被引:56
作者
Fringuelli, F [1 ]
Pizzo, F [1 ]
Tortoioli, S [1 ]
Vaccaro, L [1 ]
机构
[1] Univ Perugia, Dept Chem, I-06100 Perugia, Italy
关键词
D O I
10.1039/b303011c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title compounds were prepared via thiolysis of alkyloxiranes by arylthiols in basic aqueous medium at 30degreesC. The nucleophilic addition is anti diastereoselective and occurs on the less substituted carbon of the oxirane ring. The aqueous medium was reused and crystalline sulfides were isolated by filtration carrying out a solventless process. The protocol was used for a one-pot synthesis of hexahydrodibenzo[1,4] oxathiepinone 9.
引用
收藏
页码:436 / 440
页数:5
相关论文
共 58 条
[1]  
AIFHELI CG, 1996, SYNTHETIC COMMUN, V26, P4459
[2]  
ALBANESE D, 1994, SYNTHESIS-STUTTGART, P34
[3]   Uncatalyzed [4+2] cycloadditions of 3-nitrocoumarins with vinyl ethers in solventless conditions. A new entry to chromene derivatives [J].
Amantini, D ;
Fringuelli, F ;
Pizzo, F .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7238-7243
[4]   Efficient O-trimethylsilylation of alcohols and phenols with trimethylsilyl azide catalyzed by tetrabutylammonium bromide under neat conditions [J].
Amantini, D ;
Fringuelli, F ;
Pizzo, F ;
Vaccaro, L .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6734-6737
[5]   Water, a clean, inexpensive, and re-usable reaction medium.: One-pot synthesis of (E)-2-aryl-1-cyano-1-nitroethenes [J].
Amantini, D ;
Fringuelli, F ;
Piermatti, O ;
Pizzo, F ;
Vaccaro, L .
GREEN CHEMISTRY, 2001, 3 (05) :229-232
[6]  
Anastas P. T., 1998, GREEN CHEM THEORY PR
[7]  
APPARAO S, 1987, SYNTHESIS-STUTTGART, P896
[8]  
Attanasi OA, 2001, HELV CHIM ACTA, V84, P513, DOI 10.1002/1522-2675(20010228)84:2<513::AID-HLCA513>3.0.CO
[9]  
2-S
[10]   SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2 [J].
BEHRENS, CH ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5696-5704