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The molecular orbital (MO) calculations predict that the the reaction of the mesylate (2) of tropone oxime with nucleophiles will lead to the ring opening of the substrate. In accord with this MO prediction we have found experimentally that the facile ring opening of 2 occurs while the oxime 3 is inert to nucleophiles. Thus, 2 reacts with nucleophiles under mild conditions and gives stereoselectively...
The electric dipole moment of tropothione (1), a thiocarbonyl compound, and tropone (2), a carbonyl one, has been compared. The charge separation of 1 and 2 is evaluated on the basis of the dipole moment and ab initio calculations. The dipole moment (μ) of 1 is measured to be 4.42 D in carbon tetrachloride at -15 °C and is larger than that (μ = 3.71 D) of 2. Ab initio molecular orbital calculations...
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