- Kinetics of the ene reactions of 4-phenyl-1,2,4-triazoline-3,5-dione with β-pinene and 2-carene: Temperature, high pressure, and solvent effects
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The data on temperature, solvent, and high hydrostatic pressure influence on the rate of the ene reactions of 4-phenyl-1,2,4-triazoline-3,5-dione (1) with 2-carene (2), and β-pinene (4) have been obtained. Ene reactions 1+2 and 1+4 have high heat effects:
- Kiselev, Vladimir D.,Kornilov, Dmitry A.,Anikin, Oleg V.,Shulyatiev, Alexey A.,Kolesnikova, Anastasia O.,Konovalov, Alexander I.
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- Ene Reaction of β-Pinene with 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione: Effects of Temperature, High Pressure, and Solvent Nature
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The effects of temperature, solvent nature, and high hydrostatic pressure on the rate of the ene reaction of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione with β-pinene have been studied. The reaction gives only one product and is accompanied by a large heat effect. Comparison of the activation and reaction volumes indicates cyclic structure of the transition state. The reaction rate changes by a factor of 200 in the series of nine examined solvents, but this variation is not determined by solvent polarity.
- Kiselev,Kornilov,Anikin,Plemenkov,Konovalov
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- Reaction of 4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) with Bicyclic Monoterpenes
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The cycloaddition of the bicyclic monoterpenes camphene (4), α-pinene (5), β-pinene (6), 2-carene (7), bornene (8), and tricyclane 9 with PTAD was investigated.Only camphene and α-pinene gave rearranged urazoles (11, 14) via dipolar cycloaddition.Ene-reaction was the predominant reaction course for α-pinene (->15) and the exclusive route for β-pinene (->16) and 2-carene (->17).Steric hindrance by the gem-dimethyl group prevents cycloaddition of bornene.The cyclopropane rings in the tricyclane 9 and 2-carene are not sufficiently strained to undergo ?+2?>cycloa ddition with PTAD.None of the monoterpenes gave ?+2?>-cycloaddition.
- Adam, Waldemar,Lucchi, Ottorino De,Hill, Karlheinz
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p. 1982 - 1989
(2007/10/02)
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