FACILE SYNTHESIS OF TRIFLUOROMETHYL CARBINOLS AND TRIFLUOROMETHYL-ALPHA,BETA-UNSATURATED KETONES FROM THE NEW CF3CHO SYNTHETIC EQUIVALENT, 1,1-BIS(DIMETHYLAMINO)-2,2,2-TRIFRUOROETHANE

Authors
Citation
Yl. Xu et Wr. Dolbier, FACILE SYNTHESIS OF TRIFLUOROMETHYL CARBINOLS AND TRIFLUOROMETHYL-ALPHA,BETA-UNSATURATED KETONES FROM THE NEW CF3CHO SYNTHETIC EQUIVALENT, 1,1-BIS(DIMETHYLAMINO)-2,2,2-TRIFRUOROETHANE, Tetrahedron letters, 39(50), 1998, pp. 9151-9154
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
39
Issue
50
Year of publication
1998
Pages
9151 - 9154
Database
ISI
SICI code
0040-4039(1998)39:50<9151:FSOTCA>2.0.ZU;2-J
Abstract
1,1-Bis(dimethylamino)-2,2,2-trifluoroethane is an excellent synthetic building-block replacement for trifluoroacetaldehyde in condensation reactions with ketones using 36% aqueous HCl catalysis. Moderate to go od yields (43-68%) of trifluoromethyl carbinols are obtained with symm etric and unsymmetric methyl ketones, with the latter undergoing react ion mainly at the methyl group. Its reactions with silyl enol ethers u nder anhydrous conditions, catalyzed by ZnI2, lead directly to trifluo romethyl-alpha,beta-unsaturated ketones. (C) 1998 Elsevier Science Ltd . All rights reserved.