Rhenium catalyzed sulfurization of phosphorus(III) compounds with thiiranes: New reagents for phosphorothioate ester synthesis

被引：16

作者：

Arterburn, JB

Perry, MC

机构：

[1] Dept. of Chemistry and Biochemistry, New Mexico State University, Box 30001 / 3C, Las Cruces

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(97)10029-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the mild sulfurization of phosphorus(III) compounds with thiiranes catalyzed by ReOCl3(PPh3)(2) (I) or ReOCl3(SMe2)OPPh3) (II) is reported. The novel catalytic sulfur transfer reactions are rapid and occur efficiently under ambient conditions in organic solvents. This methodology enabled propylene sulfide to be used as a sulfurizing agent for the synthesis of a protected nucleotide phosphorothioate ester. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：7701 / 7704

页数：4

相关论文

共 30 条

[1] Catalytic transformations of thiiranes by the W(CO)(5) grouping. A new route to cyclic polydisulfides [J].

Adams, RD ;

Queisser, JA ;

Yamamoto, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10674-10675

[2] CLUSTER SYNTHESIS .25. SYNTHESIS AND CHARACTERIZATION OF NEW MIXED-METAL CLUSTER COMPLEXES BY METAL-METAL EXCHANGE - REACTIONS OF THE SULFIDO CLUSTER COMPLEXES M3(CO)9(MU-3-CO)(MU-3-S) (M = FE, RU, AND OS) WITH W(CO)5L (L = CO OR PME2PH) [J].

ADAMS, RD ;

BABIN, JE ;

MATHUR, P ;

NATARAJAN, K ;

WANG, JG .

INORGANIC CHEMISTRY, 1989, 28 (08) :1440-1445

[3]

ADAMS RD, 1997, J ORGANOMETALLICS, V16, P1430

[4] Rhenium catalyzed sulfoxide reduction [J].

Arterburn, JB ;

Perry, MC .

TETRAHEDRON LETTERS, 1996, 37 (44) :7941-7944

[5] Rhenium-catalyzed oxidation of sulfides with phenyl sulfoxide [J].

Arterburn, JB ;

Nelson, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2260-2261

[6] OXYGEN ATOM TRANSFER BETWEEN RHENIUM, SULFUR, AND PHOSPHORUS - CHARACTERIZATION AND REACTIVITY OF RE(O)CL3(ME2S)(OPPH3) AND RE(O)CL3(CNCME3)2 [J].

BRYAN, JC ;

STENKAMP, RE ;

TULIP, TH ;

MAYER, JM .

INORGANIC CHEMISTRY, 1987, 26 (14) :2283-2288

[7] STEREOSPECIFIC RHODIUM(I) CATALYZED DESULFURIZATION OF THIIRANES [J].

CALET, S ;

ALPER, H .

TETRAHEDRON LETTERS, 1986, 27 (31) :3573-3576

[8] ADSORPTION AND REACTIONS OF CYCLIC SULFIDES ON MO(110) [J].

CALHORDA, MJ ;

HOFFMANN, R ;

FRIEND, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :50-61

[9] THIIRANES - ONE-POT SYNTHESIS FROM ALKENES, AND CATALYTIC DESULFURIZATION [J].

CAPOZZI, F ;

CAPOZZI, G ;

MENICHETTI, S .

TETRAHEDRON LETTERS, 1988, 29 (33) :4177-4180

[10] Synthetic, mechanistic, and structural studies related to 1,2,4-dithiazolidine-3,5-dione [J].

Chen, L ;

Thompson, TR ;

Hammer, RP ;

Barany, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6639-6645