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For reviews, see: a, Trost, B. M, Fleming, I, Heathcock, C. H, Eds, Pergamon Press: NewYork
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For reviews, see: (a) Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: NewYork, 1991;Vol. 2, pp 527-561.
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32144450591
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For a quite different approach to the construction of the trans variant of this oxatricyclic ring system, see: Molander, G. A, Czakó, B, St. Jean, D. J, Jr. J. Org. Chem. 2006, 71, 1172-1180
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For a quite different approach to the construction of the trans variant of this oxatricyclic ring system, see: Molander, G. A.; Czakó, B.; St. Jean, D. J., Jr. J. Org. Chem. 2006, 71, 1172-1180.
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24
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75349095286
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Ph.D. Dissertation, University of California, Irvine
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Velthuisen, E. J. Ph.D. Dissertation, University of California, Irvine, 2005.
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(2005)
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Velthuisen, E.J.1
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25
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75349098679
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The preparation of cyclohexenyl iodides 10a-e is described in the Supporting Information.
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The preparation of cyclohexenyl iodides 10a-e is described in the Supporting Information.
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26
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33746485436
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The revised Pauling electronegativity of sulfur is 2.58 (similar to carbon, 2.55), whereas for oxygen it is 3.44: Allred, A. L
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The revised Pauling electronegativity of sulfur is 2.58 (similar to carbon, 2.55), whereas for oxygen it is 3.44: Allred, A. L. J. Inorg. Nucl. Chem. 1961, 17, 215-221.
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0003688717
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Springer-Verlag: Berlin, Germany, and
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Pretsch, E.; Bühlmann, P.; Affolter, C. Structure Determination of Organic Compounds; Springer-Verlag: Berlin, Germany, 2000; pp 12 and 218.
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Pretsch, E.1
Bühlmann, P.2
Affolter, C.3
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29
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75349098072
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Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 753122. An ORTEP diagram of compound 18b may be found in the Supporting Information. As is evident in this diagram, the aldehyde hydrogen atom projects close to the oxo bridge and directly into the cavity of the molecule
-
Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 753122. An ORTEP diagram of compound 18b may be found in the Supporting Information. As is evident in this diagram, the aldehyde hydrogen atom projects close to the oxo bridge and directly into the cavity of the molecule.
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30
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75349094784
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An alternate explanation for the stereoselection observed in Prins-pinacol reactions that has not yet been probed thoroughly is the possibility that the cyclization and rearrangement steps occur with some degree of concert. Computational studies to evaluate this possibility are underway
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An alternate explanation for the stereoselection observed in Prins-pinacol reactions that has not yet been probed thoroughly is the possibility that the cyclization and rearrangement steps occur with some degree of concert. Computational studies to evaluate this possibility are underway.
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31
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75349111609
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In the absence of stereoelectronic constraints, pinacol rearrangements have low activation barriers, see: (a) Bartok, M, Molnar, A. In Chemistry of Ethers, Crown Ethers, Hydroxyl Compounds and Their Sulfur Analogues; Patai, S, Ed, Wiley: New York, 1980; Part 2, pp 722-732
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In the absence of stereoelectronic constraints, pinacol rearrangements have low activation barriers, see: (a) Bartok, M.; Molnar, A. In Chemistry of Ethers, Crown Ethers, Hydroxyl Compounds and Their Sulfur Analogues; Patai, S., Ed.; Wiley: New York, 1980; Part 2, pp 722-732.
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32
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0000382638
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Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford, UK
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(b) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 3, pp 721-732.
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Rickborn, B.1
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For a particularly revealing example, see
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For a particularly revealing example, see: Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927-8940.
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Tetrahedron
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Minor, K.P.1
Overman, L.E.2
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34
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75349114077
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The three-dimensional models shown in Schemes 3 and 4 were generated by the analysis of 15-20 low-energy conformers using MMFF conformational searches (Spartan '08 for Macintosh; Wavefunction, Inc.; Irvine, CA, 2008) on cations derived from Prins cyclization of dimethyl substrates 14e and 15e, followed by DFT geometry optimization at the B3LYP/6-31G* level. Minima containing strong deformation of the carbocationic center toward a sulfur atom of the dithiane substituent or ones that could not be formed directly by the Prins reaction were disregarded.
-
The three-dimensional models shown in Schemes 3 and 4 were generated by the analysis of 15-20 low-energy conformers using MMFF conformational searches (Spartan '08 for Macintosh; Wavefunction, Inc.; Irvine, CA, 2008) on cations derived from Prins cyclization of dimethyl substrates 14e and 15e, followed by DFT geometry optimization at the B3LYP/6-31G* level. Minima containing strong deformation of the carbocationic center toward a sulfur atom of the dithiane substituent or ones that could not be formed directly by the Prins reaction were disregarded.
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35
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53649101167
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For an incisive analysis of the structure of oxocarbenium ions bearing proximal heteroatoms, and evidence against bridging from an adjacent sulfur atom to form a stable episulfonium ion intermediate, see
-
For an incisive analysis of the structure of oxocarbenium ions bearing proximal heteroatoms, and evidence against bridging from an adjacent sulfur atom to form a stable episulfonium ion intermediate, see: Beaver, M. G.; Billings, S. B.; Woerpel, K. A. Eur. J. Org. Chem. 2008, 771-781.
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Eur. J. Org. Chem
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Beaver, M.G.1
Billings, S.B.2
Woerpel, K.A.3
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0033582751
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(a) Dudley, T. J.; Smoliakova, I. P.; Hoffmann,M. R. J. Org. Chem. 1999, 64, 1247-1253.
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Alder, R. W.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960-4961.
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Alder, R.W.1
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39
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75349102414
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A similar chair preference was seen in the Prins-pinacol reaction of the configurationally analogous, structurally less elaborate, precursor (compound 16 in our earlier study).8
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8
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40
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75349097428
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22 (see the Supporting Information for details). (Chemical Equation Presented)
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22 (see the Supporting Information for details). (Chemical Equation Presented)
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41
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75349113075
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For a recent computational study and detailed discussion of the donor ability of C-H bonds to adjacent vacant p-orbitals, see ref 21b
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For a recent computational study and detailed discussion of the donor ability of C-H bonds to adjacent vacant p-orbitals, see ref 21b.
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43
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0037099465
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For reviews of 1,2-sulfur migrations, see: a
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For reviews of 1,2-sulfur migrations, see: (a) Fox, D. J.; House, D.; Warren, S. Angew. Chem., Int. Ed. 2002, 41, 2462-2482.
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(a) Saigo, K.; Hashimoto, Y.; Fang, L.; Hasegawa, M. Heterocycles 1989, 29, 2079-2082.
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0025854270
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and references cited therein
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(b) Afonso, C. A. M.; Barros, M. T.; Godinho, L. S.; Maycock, C. D. Synthesis 1991, 575-580 and references cited therein.
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Synthesis
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Afonso, C.A.M.1
Barros, M.T.2
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Maycock, C.D.4
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47
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75349092613
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The formation of products 18 is the first example of a thio-Prins-pinacol sequence in which the initial thio-Prins cyclization generates a seven-membered ring.
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The formation of products 18 is the first example of a thio-Prins-pinacol sequence in which the initial thio-Prins cyclization generates a seven-membered ring.
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48
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75349103753
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Representative experimental procedures for preparing a cyclization substrate and its rearrangement upon reaction with SnCl4. General experimental details, experimental procedures, and characterization for other new compounds can be found in the Supporting Information
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4. General experimental details, experimental procedures, and characterization for other new compounds can be found in the Supporting Information.
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49
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75349103919
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18b is highly crystalline, and after crystallization is difficult to redissolve in standard chromatography solvents
-
Byproduct 18b is highly crystalline, and after crystallization is difficult to redissolve in standard chromatography solvents. As a result, some product was lost during purification.
-
As a result, some product was lost during purification
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Byproduct1
|