TRANSITION-METAL PROMOTED ALKYLATIONS OF UNSATURATED ALCOHOLS - ALKYLATION OF ALKYNOLS WITH ORGANO-ALANES PROMOTED BY GROUP-4A METAL-CYCLOPENTADIENYL COMPOUNDS

被引:25
作者
BROWN, DC [1 ]
NICHOLS, SA [1 ]
GILPIN, AB [1 ]
THOMPSON, DW [1 ]
机构
[1] COLL WILLIAM & MARY,DEPT CHEM,WILLIAMSBURG,VA 23185
关键词
D O I
10.1021/jo01334a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Studies on the carbometalation of several alkynols, using bis(cyclopentadienyl)- and bis(methylcyclo-pentadienyl)titanium dichloride-organoalane systems, are reported. Alkynols of three types were examined: (1) HO(CH2)nC≡CH, n = 2, 3, 4; (2) HOCHRCH2C≡CH, R ≡ CH3, C2H5; and (3) HOCH2CH2C≡CR, R ≡ CH3, C2H5. Additionally, 3-butyn-l-ol was examined with bis(cyclopentadienyl)zirconium dichloride-organoalanes. Finally, the carbometalation of the trimethylsilyl ether of 3-butyn-l-ol was studied with bis(cyclopentadie-nyl)titanium dichloride-diethylaluminum chloride. All substrates react to produce substituted olefinic alcohols. © 1979, American Chemical Society. All rights reserved.
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页码:3457 / 3461
页数:5
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