REGIOCHEMICAL CONTROL IN THE REDUCTIVE CLEAVAGE OF 2-ALKYLATED OXETANES BY USE OF TRIALKYLALUMINUMS - TERTIARY ORGANOLITHIUMS WITH GAMMA-OXY FUNCTIONALITY

被引：24

作者：

MUDRYK, B ^{[1
]}

COHEN, T ^{[1
]}

机构：

[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 20期

关键词：

D O I：

10.1021/jo00020a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Whereas 2,2-dialkylated oxetanes are cleaved by lithium 4,4'-di-tert-butylbiphenylide to provide the primary organolithium-tertiary oxyanions, the same reaction in the presence of trialkylaluminums gives exclusively the 3-lithio-3,3-disubstituted propoxides, which are trapped by carbonyl compounds in moderate yields.

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页码：5760 / 5761

页数：2

相关论文

共 12 条

[1] TRANSITION-METAL CATALYZED CONJUGATE METHYLATION OF ALPHA,BETA-UNSATURATED KETONES BY TRIMETHYLALUMINUM AND LITHIUM TETRAMETHYLALUMINATE [J].

ASHBY, EC ;

HEINSOHN, G .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (22) :3297-3299

[2]

BARLUENGA J, 1985, SYNTHESIS-STUTTGART, P846

[3] ORGANOMETALLIC DERIVATIVES OF EPOXIDES [J].

BARTMANN, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (07) :653-654

[4] SYNTHETICALLY USEFUL BETA-LITHIOALKOXIDES FROM REDUCTIVE LITHIATION OF EPOXIDES BY AROMATIC RADICAL-ANIONS [J].

COHEN, T ;

JEONG, IH ;

MUDRYK, B ;

BHUPATHY, M ;

AWAD, MMA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1528-1536

[5] UNEXPECTED REGIOSELECTIVITY IN THE REDUCTIVE CLEAVAGE OF EPOXIDES - A THEORETICAL RATIONALIZATION [J].

DORIGO, AE ;

HOUK, KN ;

COHEN, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8976-8978

[6] CARBANIONS .24. REARRANGEMENTS OF (E)- AND (Z)-2,2-DIPHENYL-3-PENTENYL ALKALI-METAL COMPOUNDS [J].

GROVENSTEIN, E ;

BLACK, KW ;

GOEL, SC ;

HUGHES, RL ;

NORTHROP, JH ;

STREETER, DL ;

VANDERVEER, D .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1671-1679

[7] SKELETAL REARRANGEMENTS OF ORGANO-ALKALI METAL-COMPOUNDS [J].

GROVENSTEIN, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1978, 17 (05) :313-332

[8]

MAERCKER A, 1972, LIEBIGS ANN CHEM, V756, P43

[9] SYNTHETICALLY USEFUL DIANIONS VIA REDUCTIVE LITHIATION OF TETRAHYDROFURANS BY AROMATIC RADICAL-ANIONS [J].

MUDRYK, B ;

COHEN, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1866-1867

[10] GAMMA-LITHIOALKOXIDES VIA REDUCTIVE LITHIATION OF OXETANES BY AROMATIC RADICAL-ANIONS [J].

MUDRYK, B ;

COHEN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5657-5659