Activation of carbon-hydrogen bonds in alkanes and other organic molecules using organotransition metal complexes

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We have recently begun to investigate the interaction of C-H activating iridium and rhodium complexes with functionalized organic molecules, to determine the effect of functional groups on the process, as well as to investigate the propensity of Ir and Rh to insert into C-H versus other types of X-H bonds. Recent experiments have demonstrated that xenon liquefied at -70{degrees}C and 10 atm pressure serves as an inert solvent for the C-H oxidative addition reaction. We have been able to prepare and isolate, for the first time, C-H oxidative addition products formed from high-melting solid substrates such as naphthalene, adamantane, and … continued below

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Bergman, R.G. October 1, 1991.

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We have recently begun to investigate the interaction of C-H activating iridium and rhodium complexes with functionalized organic molecules, to determine the effect of functional groups on the process, as well as to investigate the propensity of Ir and Rh to insert into C-H versus other types of X-H bonds. Recent experiments have demonstrated that xenon liquefied at -70{degrees}C and 10 atm pressure serves as an inert solvent for the C-H oxidative addition reaction. We have been able to prepare and isolate, for the first time, C-H oxidative addition products formed from high-melting solid substrates such as naphthalene, adamantane, and even cubane; the latter case represents the first observation of C-H oxidative addition at a tertiary C-H bond. Liquid xenon has also allowed us to carry out more conveniently the C-H oxidative addition reactions of low-boiling gases that are difficult to liquefy, such as methane. Recently we have also been able to carry out analogous studies in the gas phase. Under these conditions, naked'' rather than solvated Cp*Rh(CO) is formed, and this species reacts with cyclohexane at nearly gas-kinetic rates. Under the conditions, collision between Cp*Rh(CO) and cyclohexane is the slowest step in the overall C-H activation process. In contrast, in solution association of solvent with free Cp*Rh(CO) is so rapid that the step involving C-H bond cleavage in the coordinated alkane complex becomes rate-determining. 3 refs., 5 figs.

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OSTI; NTIS; GPO Dep.

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  • American Chemical Society national meeting, San Francisco, CA (United States), 5-10 Apr 1992

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  • Other: DE92004096
  • Report No.: LBL-31443
  • Report No.: CONF-920444--8
  • Grant Number: AC03-76SF00098
  • Office of Scientific & Technical Information Report Number: 5828604
  • Archival Resource Key: ark:/67531/metadc1101624

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  • October 1, 1991

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Bergman, R.G. Activation of carbon-hydrogen bonds in alkanes and other organic molecules using organotransition metal complexes, article, October 1, 1991; [Berkeley,] California. (https://digital.library.unt.edu/ark:/67531/metadc1101624/: accessed May 31, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.

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