The Effect of a Single Fluorine Substituent On the [1,5] Homodienyl Hydrogen Shift, the Solvolytic Ring-Opening of Bromocyclopropane, And the [1,3] Carbon Shift of 6-Methylenebicyclo[3.2.0]hept-2-Ene

Cover The Effect of a Single Fluorine Substituent On the [1,5] Homodienyl Hydrogen Shift, the Solvolytic Ring-Opening of Bromocyclopropane, And the [1,3] Carbon Shift of 6-Methylenebicyclo[3.2.0]hept-2-Ene
The Effect of a Single Fluorine Substituent On the [1,5] Homodienyl Hydrogen Shift, the Solvolytic Ring-Opening of Bromocyclopropane, And the [1,3] Carbon Shift of 6-Methylenebicyclo[3.2.0]hept-2-Ene
Phanstiel, Otto, 1963-
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Standard Trans (29) cis acet. (32) trans acet. (31) 53.83 46.17 0.00 0.00 153 59.59 27.83 2.58 10.01 236 59.97 22.51 3.80 13.72 286 60.87 20.18 4.10 14.85 552 66.85 11.17 5.96 8.50 624 71.65 9.51 5.29 4.80 Temperature = 210.0°C 54.08 45.92 0.00 0.00 16 52.90 39.79 1.11 6.21 41 54.88 28.91 2.45 13.76 61 55.27 22.03 4.02 18.68 81 55.53 16.68 5.47 22.32 101 56.10 13.45 6.25 24.19 122 56.67 10.11 7.11 26.11 Temperature = 218.0°C 46.13 53.87 -- - 70 52.09 17.46 -- -- 75 54.86 15.15 -- -- 84 59.80 14....00 -- -- 93 74.44 13.84 -- -- 49 Table 4-3. The Acetolysis of cis l-bromo-2-fluoro cyclopropane (30).
Temperature = 187.0°C Time (min) Int. Standard Cis (29) cis acet. (32) trans acet. (31) 63.11 36.89 0.00 0.00 153 62.29 35.74 1.04 0.93 303 64.03 34.82 0.72 0.42 569 64.54 32.42 1.72 1.32 648 65.19 32.28 1.56 0.97 Temperature = 210.0°C 64.41 32.29 1.76 1.54 60 64.49 29.99 3.13 2.39 126 64.60 27.61 4.41 3.38 441 66.23 18.57 8.73 6.47 565 78.48 18.21 3.82 1.41 626 82.13 17.08 0.51 0.27 Temperature = 218.0°C 60.78 39.22 0.00 0.00 121 56.19 34.78 5.42 3.60 198 56.42 28.67 8.92 5.98 334 57.73 20.76 13.08 8.43 409 59.44 17.75 14.44 8.37 470 70.68 17.19 9.63 2.51 67.15 35 65.37 45 69.97 66 70.10 94 70.40 130 71.09 50 Table 4-4.


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