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For some recent examples of the synthesis of non-functionalized cyclic phosphonates, see: (a) Tasz, M. K.; Rodriguez, O. P.; Cremer, S. E.; Hussain, M. S.; Haque, M. J. Chem. Soc., Perkin Trans. 2 1996, 2221-2226.
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See also ref 3b
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(c) Brel, V. K. Synthesis 1998, 710-712. See also ref 3b.
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Brel, V.K.1
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Moriarty, R. M.; Tao, A.; Condeiu, C.; Gilardi, R. Tetrahedron Lett. 1997, 38, 2597-2600.
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0042773327
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note
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31P NMR spectra of the crude reaction mixtures.
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27
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0042773328
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note
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Reaction in pure THF gave lower selectivity (3.5:1). Reaction in DME, without HMPA, was sluggish and did not go to completion.
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28
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0042272211
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note
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The relative stereochemistry of this compound was determined by single-crystal X-ray crystallography.
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29
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0001451148
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(a) Murray, R. W.; Singh, M.; Williams, B. L.; Moncrieff, H. M. J. Org. Chem. 1996, 61, 1830-1841.
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0009517455
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(b) For a comparative study of oxidations using DMD and TFD, see: Adam, W.; Paredes, R.; Smerz, A. K.; Veloza, L. A. Eur. J. Org. Chem. 1998, 349-354.
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31
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0000050003
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For examples of the syn-directing effect of a carbonyl group in DMD epoxidations, see: (a) Bovicelli, P.; Lupattelli, P.; Mincione, E.; Prencipe, T.; Curci, R. J. Org. Chem. 1992, 57, 2182-2184. (b) See also ref 10a, Table 3.
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0042773325
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note
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Displacement of the phenoxy group in acyclic mixed phenyl phosphonates occurs with inversion of the configuration; see ref 6.
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37
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0000894454
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(a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943-3946.
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Donohoe, T.J.1
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40
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0041771425
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Attempts to deprotect the free diol led to decomposition
-
Attempts to deprotect the free diol led to decomposition.
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41
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85022880129
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Deprotection with CAN gave considerably lower yields. For oxidation of 1,4-dimethoxybenzene in the presence of pyridinecarboxylic acids, see: Syper, L.; Klock, K. Mlochowski, J.; Szulc, Z. Synthesis 1979, 36, 123-129. Syper, L.; Mlochowski, J. Tetrahedron 1980, 521-522.
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0042272210
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Deprotection with CAN gave considerably lower yields. For oxidation of 1,4-dimethoxybenzene in the presence of pyridinecarboxylic acids, see: Syper, L.; Klock, K. Mlochowski, J.; Szulc, Z. Synthesis 1979, 36, 123-129. Syper, L.; Mlochowski, J. Tetrahedron 1980, 521-522.
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47
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0043274630
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note
-
It is worth noting that attempts for dihydroxylation without citric acid gave only unreacted starting material.
-
-
-
-
48
-
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0042272209
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note
-
Donohoe attributed the difference in selectivity to the orientation of the hydroxyl group; the trans-isomer bearing a locked axial hydroxy group gave higher selectivity.
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