References
- Chung , S.-K. and Filmore , K. L. 1983 . J. Chem. Soc. Chem. Comm , Evidence for electron-transfer in metal hydride reductions of organic halides:, 358–359 andAshby, E. C.; DePriest, R. N.; Goel, A. B. Tetrahedron Lett. 1981, 22, 1763–1766.
- Brown , H. C. and Krishnamurthy , S. 1973 . J. Am. Chem. Soc. , 95 : 1669
- Numan , H. and Wynberg , H. 1978 . J. Org. Chem. , These results stand in contrast to the smooth displacement of methanesulfonate from 4(a)-methylsulfonyloxyadamantan-2-one by LiA1D4/ether with inversion of stereochemistry., 43, 2232.
- Masamune , S. , Rossy , P. A. and Bates , G. S. 1973 . J. Am. Chem. Soc. , 95 : 6452 We thank Professor Masamune for experimental details of the preparation of LiA1H(OCH3)-CuI.
- Lightner , D. A. , Chang , T. C. and Horwitz , J. 1977 . Tetrahedron Lett. 3019; 1978, 696.
- Snatzke , G. and Eckhardt , G. 1968 . Tetrahedron , 24 : 4543
- Equatorial and axial in the adamantanone system refer to the carbonyl bearing six-membered ring(s).
- Hunsdiecker reaction on the axial COOH epimer of 12 gave only very poor isolated yields of bromoketones.
- Stothers , J. B. and Tan , C. T. 1974 . J. Chem. Soc. Chem. Comm. , 738. [Pr(fod)3].See also Karhan, J., Hajek, M., Mohyla, I. Ksandr, Z. and Vodicka, L., Coll. Czech Chem. Comm., 1979, 44, 533 [Eu(fod)3-d27 and Abraham, R. J., Chadwick, D. J., and Sancassun, F., Tetrahedron, 1981, 37, 108 [Yb(fod)3].
- Eu(fod)3 shifts the [btilde]-axial hydrogens more downfield. The reaction product of 7 exhibited an integrated ratio of 1.24:1 for the axial : equatorial hydrogens. This corresponds to a ratio of 3.96 [btilde]-Ha: 3.04 [btilde]-He, after correction for 15% do-adamantanone. aThe reaction product of 8 exhibited an integrated raio of only 1.06 : 1 for the axial : equational hydrogens, corresponding to a ratio of 3.62 [btilde]-H to 3.38 [btilde]-He, after correction for 15% do-adamantanone.
- Snatzke , G. and Eckhardt , G. 1968 . Chem. Ber. , 101 : 2010
- Snatzke , G. and Marquarding , D. 1967 . Chem. Ber. , 100 : 1710