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For recent transformations of the carbonyl group with DAST, see: (a) Giardina, G.; Dondio, G.; Grugni, M. Synlett 1995, 55. (b) Ando, K.; Koike, F.; Kondo, F.; Takayama, H. Chem. Pharm. Bull. 1995, 43, 189. (c) Sabol, J. S.; Brake, N. W.; McDonald, I. A. Tetrahedron Lett. 1994, 35, 1821.
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19F NMR spectrum of the crude product mixture.
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Rearrangements of ethers of simple tertiary allylic alcohols occur with low stereoselectivity because 1,3-repulsions raise the energies of all the possible transition states, converging them. (a) See ref 28. There are exceptions to this general statement which rely on additional organizing interactions. For example, see: (b) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 753.
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Rearrangements of ethers of simple tertiary allylic alcohols occur with low stereoselectivity because 1,3-repulsions raise the energies of all the possible transition states, converging them. (a) See ref 28. There are exceptions to this general statement which rely on additional organizing interactions. For example, see: (b) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1993, 34, 753.
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