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Rearrangements and fragmentations
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8
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Degenerate carbocation rearrangements
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(h) Ahlberg, P.; Jonsall, G.; Engdahl, C. Degenerate Carbocation Rearrangements. In Advances in Physical Organic Chemistry; Gold, V., Bethell, D., Eds.; Academic Press: London, 1983; Vol. 19, pp 223-379.
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18
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21
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23
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3142599316
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note
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The pseudo-boat conformation can be anticipated by the dihedral angle (θ) of 172.3° for the linkage of O(1)-C(8)-C(14)-C(4) and -178.7° for O(2)-C(12)-C(4)-C(14), respectively; see Figure 1.
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24
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3142533036
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note
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This is reflected in the smaller dihedral angle (θ) of 109.2° for the C(15)-C(4)-C(14)-C(8) linkage involving cyclobutene σ-bond as compared to 135.3° for the C(8)-C(14)-C(4)-C(26) linkage involving the quinone methyl substituent; see Figure 1.
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25
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0004293179
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(a) Kirby, A. J. Stereoelectronic Effects; Oxford University Press, Inc.: New York, 1966.
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0009742574
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(e) Brown, H. C.; Ravindranathan, M.; Peters, E. N. J. Am. Chem. Soc. 1974, 96, 7351.
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Peters, E.N.3
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3142607332
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(f) Brown, H. C.; Ikegami, S.; Liy, K.-T.; Tritle, G. L. J. Am. Chem. Soc. 1976, 98, 2531.
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Tritle, G.L.4
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35
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0025280370
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36
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3142609417
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note
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4 are rather complicated because of their strong tendency to form the 2:1 complexes and the 1:1 dimeric complexes, satisfying the desire of Ti and Sn for hexacoordination; see ref 18.
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37
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3142539224
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note
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The transoid binding may allow the favorable σ*-σ interaction between the coordination σ* bond and the adjacent cyclopropane connecting σ-bond. Such an orbital interaction will intensify the electron demand of the relevant bond, which results in the promotion of the cyclopropane ring cleavage; see ref 7.
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39
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15644378136
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(b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C. Chem. Rev. 1989, 89, 165.
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Yip, Y.-C.4
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40
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0000829062
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(a) Wilcox, C. F.; Loew, L. M.; Hoffmann, R. J. Am. Chem. Soc. 1973, 95, 8192.
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Wilcox, C.F.1
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Hoffmann, R.3
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41
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0010441251
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(b) Harmony, M. D.; Mathur, S. N.; Choe, J.-I.; Kattija-Ari, M.; Howard, A. E.; Staley, S. W. J. Am. Chem. Soc. 1981, 103, 2961.
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Harmony, M.D.1
Mathur, S.N.2
Choe, J.-I.3
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Howard, A.E.5
Staley, S.W.6
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42
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84985166063
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(c) Jason, M. E.; Gallucci, J. C.; Ibers, J. A. Isr. J. Chem. 1981, 21, 95.
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Jason, M.E.1
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43
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0001390695
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Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801.
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Childs, R.F.1
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Nixon, A.3
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44
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3142603353
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note
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Incidentally, the isolated 4bα was easily transformed into the intramolecular [2 + 2] photoadduct on irradiation with a 300 W high-pressure mercury lamp. Details will be described elsewhere.
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45
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0001693455
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4 is well-known and confirmed in crystal structures of the complexes with ethyl acetate and ethyl anisate. For example, see: (a) Brun, L. Acta Crystallogr. 1966, 20, 739.
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Acta Crystallogr.
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Brun, L.1
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46
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0000649960
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(b) Bassi, I. W.; Calcaterra, M.; Intrito, R. J. Organomet. Chem. 1977, 127, 305.
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Bassi, I.W.1
Calcaterra, M.2
Intrito, R.3
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47
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0001186548
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Carlson, R.; Lundstedt, T.; Nordahl, Å.; Prochazka, M. Acta Chem. Scand. 1986, B40, 522.
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Carlson, R.1
Lundstedt, T.2
Nordahl, Å.3
Prochazka, M.4
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48
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84986550210
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3 (-1.24), Et (-1.31), Bu (-1.63), and Ph (-3.79). See: Unger, S. H.; Hansch, C. Prog. Phys. Org. Chem. 1976, 12, 91.
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Unger, S.H.1
Hansch, C.2
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