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The experimental details for the synthesis of 3 are contained in the Supporting Information.
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The experimental details for the synthesis of 3 are contained in the Supporting Information.
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10
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0011985659
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This is approximately 3 kcal mol-1 lower than 2. In general, the benzannulated forms of such conjugated cycles are more stable than their unsubstituted forms; see for example: F. Sondheimer, Acc. Chem. Res. 1972, 5, 81-91
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-1 lower than 2. In general, the benzannulated forms of such conjugated cycles are more stable than their unsubstituted forms; see for example: F. Sondheimer, Acc. Chem. Res. 1972, 5, 81-91.
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11
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1542744425
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Substituted versions of 2 have been invoked as intermediates and transient photoproducts, see: a E. H. White, E. W. Friend, R. L. Stern, H. Maskill, J. Am. Chem. Soc. 1969, 91, 523-525;
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Substituted versions of 2 have been invoked as intermediates and transient photoproducts, see: a) E. H. White, E. W. Friend, R. L. Stern, H. Maskill, J. Am. Chem. Soc. 1969, 91, 523-525;
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From analysis of the crude reaction mixture, we also observe other byproducts which appear to be oligomers containing both cis and trans double bonds. See also: H. Meier, Synthesis 2002, 9, 1213-1228.
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From analysis of the crude reaction mixture, we also observe other byproducts which appear to be oligomers containing both cis and trans double bonds. See also: H. Meier, Synthesis 2002, 9, 1213-1228.
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84980091803
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The two enantiomers of trans-cyclooctene have been resolved using chiral silver salts: A. C. Cope, C. R. Ganellin, H. W. Johnson, T. V. Van Auken, H. J. S. Winkler, J. Am. Chem. Soc. 1963, 85, 3276-3279.
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The two enantiomers of trans-cyclooctene have been resolved using chiral silver salts: A. C. Cope, C. R. Ganellin, H. W. Johnson, T. V. Van Auken, H. J. S. Winkler, J. Am. Chem. Soc. 1963, 85, 3276-3279.
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25
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0001567777
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IR stretching vibrations matching those seen in reference [9] were seen again by Griffin et al. (see: C. E. Griffin, J. A. Peters, J. Org. Chem. 1963, 28, 1715-1716) using the bis-Wittig reaction described herein.
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IR stretching vibrations matching those seen in reference [9] were seen again by Griffin et al. (see: C. E. Griffin, J. A. Peters, J. Org. Chem. 1963, 28, 1715-1716) using the bis-Wittig reaction described herein.
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27
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53549121069
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The Supporting Information contains the crystallographic information file (.cif). CCDC-676888 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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The Supporting Information contains the crystallographic information file (.cif). CCDC-676888 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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13C satellites, but the coupling constants were similar (16 Hz versus 14.8 Hz). However, an NOE signal between the most upfield olefin signal and an ortho proton of the phenyl ring confirmed that it corresponds to the cis olefinic proton. This is in agreement with the assignment made by analogy to the cis olefin in the planar tribenzocyclooctatetraene (at δ = 5.91 ppm), see: X. Wang, X. Hou, Z. Zhou, T. C. W. Mak, H. N. C. Wong, J. Org. Chem. 1993, 58, 7498-7506.
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13C satellites, but the coupling constants were similar (16 Hz versus 14.8 Hz). However, an NOE signal between the most upfield olefin signal and an ortho proton of the phenyl ring confirmed that it corresponds to the cis olefinic proton. This is in agreement with the assignment made by analogy to the cis olefin in the planar tribenzocyclooctatetraene (at δ = 5.91 ppm), see: X. Wang, X. Hou, Z. Zhou, T. C. W. Mak, H. N. C. Wong, J. Org. Chem. 1993, 58, 7498-7506.
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The Supporting Information contains the optimized structure for 3 and the cis,cis isomer, each generated using DFT. The calculations were performed using Jaguar (v. 6.0 and 6.5) with the B3LYP functional, Schrödinger, L. L. C., Portland, OR, 1991-2005. The geometries were optimized using the 6-31G** basis sets, and the energy difference between the two isomers was calculated using the 6-311G** basis sets.
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The Supporting Information contains the optimized structure for 3 and the cis,cis isomer, each generated using DFT. The calculations were performed using Jaguar (v. 6.0 and 6.5) with the B3LYP functional, Schrödinger, L. L. C., Portland, OR, 1991-2005. The geometries were optimized using the 6-31G** basis sets, and the energy difference between the two isomers was calculated using the 6-311G** basis sets.
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