Camphor → Borneol
Reaktionsgleichung
[2H-].[Al+3].[Li+].[2H-].[2H-].[2H-].[C:7]12([CH3:17])[C:14]([CH3:16])([CH3:15])[CH:11]([CH2:12][CH2:13]1)[CH2:10][C:8]2=[O:9].[H-]>CCOCC>[CH3:15][C:14]1([CH3:16])[C:7]2([CH3:17])[CH:8]([OH:9])[CH2:10][CH:11]1[CH2:12][CH2:13]2Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a slurry of lithium aluminum deuteride (LiAlD4) (0.012 g) in anhydrous ether (1 mL) was added, with stirring, camphor (0.1 g) in ether (2 mL), followed by heating at reflux for 3 hours. After cooling to room temperature, the excess hydride was decomposed by addition of moist ether, then the organic layer was washed with brine, dried (Na2CO4) and evaporated to give a quantitative yield of deuteriated isoborneol (0.1 g). 2H NMR (hexanes): δ 3.75. See B. Belleau, J. Am. Chem. Soc., 82, p. 5751 (1960).