Availability and reactivity of concentrated dimethyldioxirane solutions in solvents other than acetone

被引：38

作者：

Gibert, M ^{[1
]}

Ferrer, M ^{[1
]}

SanchezBaeza, F ^{[1
]}

Messeguer, A ^{[1
]}

机构：

[1] CSIC,CID,DEPT BIOL ORGAN CHEM,ES-08034 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(97)00533-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four to five-fold increase in concentration or the possibility of isolation in ''acetone-free'' medium has become possible for dimethyldioxirane solutions in CH2Cl2, CHCl3, CCl4 and CFCl3 by employing a simple work-up procedure which involved washings with phosphate buffer. This procedure allowed the kinetics of the epoxidation of cis-stilbene to be studied and which were shown to follow a simple second order rate law for all solvents studied. The relative reaction rates were as follows: acetic acid > CHCl3 > acetone > CCl4 > toluene > ethyl acetate. (C) 1997 Elsevier Science Ltd.

引用

页码：8643 / 8650

页数：8

共 15 条

[1] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].

ADAM, W ;

CHAN, YY ;

CREMER, D ;

GAUSS, J ;

SCHEUTZOW, D ;

SCHINDLER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803

[2] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[3] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

[4] EPOXIDATION BY DIMETHYLDIOXIRANE - ELECTRONIC AND STERIC EFFECTS [J].

BAUMSTARK, AL ;

VASQUEZ, PC .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3437-3439

[5] EPOXIDATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY DIMETHYLDIOXIRANE [J].

BAUMSTARK, AL ;

HARDEN, DB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7615-7618

[6] Oxyfunctionalization of (5 beta)-bile acids by dimethyldioxirane: Hydroxylation at C-5, C-14, and C-17 [J].

Cerre, C ;

Hofmann, AF ;

Schteingart, CD ;

Jia, WP ;

Maltby, D .

TETRAHEDRON, 1997, 53 (02) :435-446

[7] DIOXIRANE OXIDATIONS - TAMING THE REACTIVITY-SELECTIVITY PRINCIPLE [J].

CURCI, R ;

DINOI, A ;

RUBINO, MF .

PURE AND APPLIED CHEMISTRY, 1995, 67 (05) :811-822

[8] DECOMPOSITION OF DIOXIRANES INDUCED BY DIALKYL ETHERS [J].

FERRER, M ;

SANCHEZBAEZA, F ;

CASAS, J ;

MESSEGUER, A .

TETRAHEDRON LETTERS, 1994, 35 (18) :2981-2984

[9] Easy availability of more concentrated and versatile dimethyldioxirane solutions [J].

Ferrer, M ;

Gibert, M ;

SanchezBaeza, F ;

Messeguer, A .

TETRAHEDRON LETTERS, 1996, 37 (20) :3585-3586

[10]

Murray R.W., 1990, J CHEM SOC P2, V2, P349

← 1 2 →