SODIUM SULFIDE AS A MILD AND SELECTIVE DESILYLATING REAGENT

被引：13

作者：

SCHMITTBERGER, T ^{[1
]}

UGUEN, D ^{[1
]}

机构：

[1] ECOLE EUROPEENNE HAUTES ETUDES IND CHIM,CNRS,SYNTH ORGAN LAB,F-67008 STRASBOURG,FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 41期

关键词：

D O I：

10.1016/0040-4039(95)01549-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

diphenyl-t-butoxysilyl (i.e. DPTBOS) derivatives of alcohols are selectively cleaved by nonahydrated sodium sulphide in ethanol, the order of reactivity being: primary approximate to secondary>>tertiary. The corresponding t-butyldimethylsilyl and diphenyl-t-butylsilyl derivatives remain unaffected in these conditions.

引用

页码：7445 / 7448

页数：4

共 8 条

[1] MECHANISMS OF SOLVOLYSIS OF ORGANOSILICON COMPOUNDS CONTAINING BONDS FROM SILICON TO OXYGEN, NITROGEN, AND CARBON [J].

BOE, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 107 (02) :139-217

[2] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[3] HYPERVALENT SPECIES OF SILICON - STRUCTURE AND REACTIVITY [J].

CORRIU, RJP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 400 (1-2) :81-106

[4] CONCERNING THE MECHANISM FOR BIFUNCTIONAL CATALYSIS IN THE METHANOLYSIS OF METHOXYMETHYLPHENOXYPHENYLSILANE [J].

DIETZE, PE .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5653-5662

[5]

GASMANN PG, 1989, J AM CHEM SOC, V111, P2652

[6] SYMMETRICAL ALKOXYSILYL ETHERS - A NEW CLASS OF ALCOHOL-PROTECTING GROUPS - PREPARATION OF TERT-BUTOXYDIPHENYLSILYL ETHERS [J].

GILLARD, JW ;

FORTIN, R ;

MORTON, HE ;

YOAKIM, C ;

QUESNELLE, CA ;

DAIGNAULT, S ;

GUINDON, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2602-2608

[7] PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].

HANESSIAN, S ;

LAVALLEE, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977

[8] SYNTHETIC METHODS AND REACTIONS .71. CHLOROTRIMETHYLSILANE LITHIUM SULFIDE AND TERT-BUTYLDIMETHYLSILYL CHLORIDE LITHIUM SULFIDE, MILD AND EFFICIENT SILYLATING REAGENTS [J].

OLAH, GA ;

GUPTA, BGB ;

NARANG, SC ;

MALHOTRA, R .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4272-4275

← 1 →