W. Dmowski, K. Piasecka-Maciejewska
Jul 20, 1999
Citations
0
Influential Citations
8
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Treatment of (1 S ,4 R )-(−)-camphanic acid ( 1 ) with sulphur tetrafluoride affords (1 R ,4 S )-(−)-3-oxa-4-(trifluoromethyl)camphor ( 2 ) as a main product together with small amounts of (1 S ,4 R )-camphanoyl fluoride ( 3 ), (1 R )-3-(trifluoromethyl)camphonenoyl fluoride ( 4 ) and (1 R )-3,4-dehydrocamphoroyl difluoride ( 5 ). Reduction of 2 with LiAlH 4 gives the diol, (1 R ,3 S )-(+)-3-hydroxy-1,2,2-trimethyl-3-trifluoromethyl-1-cyclopentanemethanol ( 6 ), which when heated with KHSO 4 readily dehydrates to (1 R ,4 S )-(−)-3-oxa-4-(trifluoromethyl)bornane ( 7 ). Acylation of the diol 6 proceeds regioselectively at the primary hydroxyl group to give exclusively monoacylated derivative 8 .