Nucleophilic reactions between cyclic 1,2-sulfites and chloride ions

被引:7
作者
Nymann, K [1 ]
Jensen, L [1 ]
Svendsen, JS [1 ]
机构
[1] UNIV TROMSO,INST MATH & PHYS SCI,DEPT CHEM,N-9037 TROMSO,NORWAY
来源
ACTA CHEMICA SCANDINAVICA | 1996年 / 50卷 / 09期
关键词
D O I
10.3891/acta.chem.scand.50-0832
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohydrins are formed with low regio and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochemical outcome of the reactions. The results showed that reversible inversion pathways (S(N)2 reactions) and a retention pathway (S(N)2i reaction) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites.
引用
收藏
页码:832 / 841
页数:10
相关论文
共 26 条
[1]   THE DECOMPOSITION OF SECONDARY ALKYL CHLOROSULFITES .2. SOLVENT EFFECTS AND MECHANISMS [J].
BOOZER, CE ;
LEWIS, ES .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (13) :3182-3186
[2]   PARA-CARBOXYSTYRENE - WITTIG PROCEDURE IN AQUEOUS-MEDIUM [J].
BROOS, R ;
TAVERNIER, D ;
ANTEUNIS, M .
JOURNAL OF CHEMICAL EDUCATION, 1978, 55 (12) :813-813
[4]   CHEMISTRY OF CYCLOPROPANOLS .5. STEREOCHEMISTRY OF ACID- AND BASE-CATALYZED RING OPENING [J].
DEPUY, CH ;
BREITBEI.FW ;
DEBRUIN, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3347-&
[5]   VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE [J].
GAO, Y ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7538-7539
[6]   A PRACTICAL SYNTHESIS OF D-MALATE ESTERS FROM L-TARTRATE ESTERS [J].
GAO, Y ;
ZEPP, CM .
TETRAHEDRON LETTERS, 1991, 32 (27) :3155-3158
[7]   PREPARATION AND HYDROLYSIS OF SOME ACETALS AND ESTERS OF D(-)-2,3-BUTANEDIOL [J].
GARNER, HK ;
LUCAS, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (12) :5497-5501
[8]   SUBSTITUTION OF OSIDIC CYCLIC SULFITES BY THE NITROGEN ION [J].
GUILLER, A ;
GAGNIEU, CH ;
PACHECO, H .
TETRAHEDRON LETTERS, 1985, 26 (51) :6343-6344
[9]   ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].
JACOBSEN, EN ;
MARKO, I ;
MUNGALL, WS ;
SCHRODER, G ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970
[10]  
Johnson R.A., 1993, CATALYTIC ASYMMETRIC