Alkoxides of o-silyl benzyl alcohols in cleavage reactions:: approaches to benzyl and silyl anion equivalents

被引：22

作者：

Hudrlik, PF ^{[1
]}

Arango, JO

Hijji, YM

Okoro, CO

Hudrlik, AM

机构：

[1] Howard Univ, Dept Chem, Washington, DC 20059 USA

[2] Morgan State Univ, Dept Chem, Baltimore, MD 21251 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2000年 / 78卷 / 11期

关键词：

silyl migration; benzyl anion equivalent; silyl anion equivalent; beta-silyl ketone; gamma-hydroxysilane;

D O I：

10.1139/cjc-78-11-1421

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The alkoxides of o-silyl benzyl alcohols 4 undergo cleavage reactions under mild conditions allowing transfer of a benzyl or silyl group to an electrophile. Reactions 3a --> 8, and 3c or 4c --> 11 illustrate their potential as benzyl and silyl anion equivalents.

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收藏

页码：1421 / 1427

页数：7

相关论文

共 37 条

[11] OXIDATION OF ALKENYLDISILANES BY META-CHLOROPERBENZOIC ACID [J].

DIXON, TA ;

STEELE, KP ;

WEBER, WP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 231 (04) :299-305

[12]

EGOROV YP, 1963, B ACAD SCI USSR CH, P515

[13] CORRELATION BETWEEN REACTIVITY OF THE 1-CARBON ATOM IN ALCOHOLS, AND CERTAIN PROPERTIES OF ALKOXYSILANES [J].

GERRARD, W ;

KILBURN, KD .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JUN) :1536-1539

[14] Rearrangement of o-(chloromethyldimethylsilyl)phenylmethoxide: evidence for an apical position of the migrating group in a trigonal bipyramid intermediate [J].

Hijji, YM ;

Hudrlik, PF ;

Hudrlik, AM .

CHEMICAL COMMUNICATIONS, 1998, (11) :1213-1214

[15] Preparation of o-(silyl)benzyl alcohols [J].

Hijji, YM ;

Hudrlik, PF ;

Okoro, CO ;

Hudrlik, AM .

SYNTHETIC COMMUNICATIONS, 1997, 27 (24) :4297-4308

[16] SYNTHESIS OF BETA-SILYL KETONES VIA REACTION OF TRIMETHYLSILYLLITHIUM WITH UNSATURATED HYDRAZONES - APPLICATION TO THE SYNTHESIS OF BREVICOMIN [J].

HUDRLIK, PF ;

HUDRLIK, AM ;

YIMENU, T ;

WAUGH, MA ;

NAGENDRAPPA, G .

TETRAHEDRON, 1988, 44 (13) :3791-3803

[17]

HUDRLIK PF, 1982, J AM CHEM SOC, V104, P1157, DOI 10.1021/ja00368a609

[18] EFFECT OF TRIMETHYLSILYL GROUPS ON BECKMANN REARRANGEMENTS AND FRAGMENTATIONS [J].

HUDRLIK, PF ;

WAUGH, MA ;

HUDRLIK, AM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 271 (1-3) :69-76

[19] GENERATION OF ANIONIC INTERMEDIATES BY INTRAMOLECULAR NUCLEOPHILIC-ATTACK AT SILICON [J].

HUDRLIK, PF ;

ABDALLAH, YM ;

HUDRLIK, AM .

TETRAHEDRON LETTERS, 1992, 33 (45) :6747-6750

[20] SILICON-DIRECTED BAEYER-VILLIGER REACTIONS - STEREOSPECIFIC SYNTHESIS OF OLEFINIC ACIDS AND ESTERS [J].

HUDRLIK, PF ;

HUDRLIK, AM ;

NAGENDRAPPA, G ;

YIMENU, T ;

ZELLERS, ET ;

CHIN, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (22) :6894-6896

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