Nucleophilic ring opening of 1,2-epoxides in aqueous medium

被引：41

作者：

Amantini, D ^{[1
]}

Fringuelli, F ^{[1
]}

Piermatti, O ^{[1
]}

Tortoioli, S ^{[1
]}

Vaccaro, L ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim, Via Elce Sotto 8, I-06100 Perugia, Italy

来源：

ARKIVOC | 2002年

关键词：

1,2-epoxides; azidolysis; hydrolysis; thiolysis; Lewis-acid catalysts;

D O I：

10.3998/ark.5550190.0003.b26

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic ring opening of 1,2-epoxides in aqueous medium in the presence and absence of metal salts is reviewed. Azidolysis, hydrolysis, iodolysis and thiolysis are the reactions mainly investigated. The pH of the reaction medium controls the reactivity and regioselectivity of the process. By working at suitable pH values, even salts such as AlCl3, SnCl4 and TiCl4 are active catalysts.

引用

页码：293 / 311

页数：19

共 51 条

[1] CYCLIZATION AND SUBSEQUENT REACTIONS OF 2'-HYDROXY-6'-METHOXYCHALCONE EPOXIDE AND RELATED-COMPOUNDS
ADAMS, CJ
MAIN, L
[J]. TETRAHEDRON, 1991, 47 (27) : 4979 - 4990
[2] Bromolysis and iodolysis of α,β-epoxycarboxylic acids in water catalyzed by indium halides
Amantini, D
Fringuelli, F
Pizzo, F
Vaccaro, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) : 4463 - 4467
[3] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .11. RING-OPENING REACTIONS OF ALIPHATIC MONOFUNCTIONALIZED AND DIFUNCTIONALIZED CIS AND TRANS 2,3-EPOXY AND 3,4-EPOXY ESTERS
AZZENA, F
CROTTI, P
FAVERO, L
PINESCHI, M
[J]. TETRAHEDRON, 1995, 51 (48) : 13409 - 13422
[4] Regio- and stereo-chemical outcomes in the nucleophilic ring-cleavage reactions of mono-epoxides derived from cis-1,2-dihydrocatechols
Banwell, MG
Haddad, N
Hudlicky, T
Nugent, TC
Mackay, MF
Richards, SL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12): : 1779 - 1791
[5] A SIMPLE 2-STRUCTURE MODEL FOR LIQUID WATER
BENSON, SW
SIEBERT, ED
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) : 4269 - 4276
[6] Bröll D, 1999, ANGEW CHEM INT EDIT, V38, P2999
[7] Brufola G, 1997, HETEROCYCLES, V45, P1715
[8] Brufola G, 1996, HETEROCYCLES, V43, P1257
[9] TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING
CARON, M
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) : 1557 - 1560
[10] EFFICIENT METAL SALT CATALYZED AZIDOLYSIS OF EPOXIDES WITH SODIUM-AZIDE IN ACETONITRILE
CHINI, M
CROTTI, P
MACCHIA, F
[J]. TETRAHEDRON LETTERS, 1990, 31 (39) : 5641 - 5644

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