The kinetics of pyrolysis of 1,3,3-trimethylcyclopropene. Evidence for the involvement of alkylidene carbenes in the thermal isomerisation of cyclopropenes
作者： Robin Walsh , Christian Wolf , Sven Untiedt , Armin de Meijere
DOI: 10.1039/C39920000421
关键词: Kinetics 、 Photochemistry 、 Reaction rate constant 、 Hydrocarbon 、 Chemistry 、 Carbene 、 Isomerization 、 Yield (chemistry) 、 Pyrolysis
摘要: A low yield of 4-methylpent-2-yne in the gas-phase isomerisation 1,3,3-trimethylcyclopropene is shown to be more consistent with an alkylidene carbene transient than a, 1,3-biradical intermediate.
rsc.org
sci-hub.se 参考文章(13)
M. Yoshimine, J. Pacansky, N. Honjou, Ab initio studies of the C3H4 surface. 3. Thermal isomerization Journal of the American Chemical Society. ,vol. 111, pp. 4198- 4209 ,(1989) , 10.1021/JA00194A008
J.H. Kiefer, S.S. Sidhu, S.S. Kumaran, E.A. Irdam, RRKM model of C2H4 dissociation: Heat of formation of vinylidene Chemical Physics Letters. ,vol. 159, pp. 32- 34 ,(1989) , 10.1016/S0009-2614(89)87448-2
Paul Davison, H.Monty Frey, Robin Walsh, Vinylidene: probable intemediacy in methylenecyclopropane decomposition and heat of formation Chemical Physics Letters. ,vol. 120, pp. 227- 228 ,(1985) , 10.1016/0009-2614(85)87045-7
R. F. C. Brown, Thermal rearrangements of alkynes under FVP conditions. the acetylene-methylenecarbene rearrangement Recueil des Travaux Chimiques des Pays-Bas. ,vol. 107, pp. 655- 661 ,(2010) , 10.1002/RECL.19881071202
Robin Walsh, Sven Untiedt, Michael Stohlmeier, Armin de Meijere, Gas‐Phase Kinetics of Pyrolysis of 3,3‐Dimethylcyclopropene and Its 1‐Trimethylsilyl Derivative The Effect of Silyl Substitution on Cyclopropene Isomerisation Chemische Berichte. ,vol. 122, pp. 637- 642 ,(1989) , 10.1002/CBER.19891220409
J. A. Pople, Potential surfaces for simple rearrangements Pure and Applied Chemistry. ,vol. 55, pp. 343- 346 ,(1983) , 10.1351/PAC198855020343
Yoshihiro Osamura, Henry F. Schaefer, Stephen K. Gray, William H. Miller, Vinylidene: a very shallow minimum on the C2H2 potential energy surface Journal of the American Chemical Society. ,vol. 103, pp. 1904- 1907 ,(1981) , 10.1021/JA00398A005
Andreas Brandl, Heinrich Nöth, Beiträge zur Chemie des Bors, 161. Reaktionen protonenaktiver Verbindungen mit (tert‐Butylimino)(2,2,6,6‐tetramethylpiperidino)boran Chemische Berichte. ,vol. 118, pp. 3759- 3770 ,(1985) , 10.1002/CBER.19851180928
Eunice J. York, Wolfgang. Dittmar, J. Ronald. Stevenson, Robert G. Bergman, Synthesis of an optically active cyclopropene and kinetics of its thermal racemization in the gas phase. Intermediacy of a vinylcarbene Journal of the American Chemical Society. ,vol. 95, pp. 5680- 5687 ,(1973) , 10.1021/JA00798A038
R. P. Duran, V. T. Amorebieta, A. J. Colussi, Pyrolysis of acetylene: a thermal source of vinylidene Journal of the American Chemical Society. ,vol. 109, pp. 3154- 3155 ,(1987) , 10.1021/JA00244A053