Y. Habata, J. Bradshaw, R. W. Nelson
Mar 24, 1997
Citations
0
Influential Citations
2
Citations
Journal
Tetrahedron
Abstract
Abstract Treatment of 1,8-dichloroanthraquinone with ( S )-(−)-2-(tetrahydropyranyloxy)-1-propanol in the presence of NaH in THF gave monosubstituted-monodechlorinated product 2 and the desired 1,8-disubstituted product 1 . Molecular mechanics calculations and 1 H NMR experiments suggest that the tetrahydropyranyl group in the side chain of monosubstituted-monochloro product 3 binders the second reaction site and the Na + cation interacts with the oxygen atoms of the side chain and ketone function allowing the hydride anion access to the second reaction site.