Substituent effects in heterogeneous catalysis. VIII. Reactions of 2-methyl- and 2-ethylcyclohexanone with deuterium catalyzed by platinum metals

Teratani, S; Tanaka, K; Ogawa, H; Taya, K

doi:10.1016/0021-9517(81)90346-8

Title: Substituent effects in heterogeneous catalysis. VIII. Reactions of 2-methyl- and 2-ethylcyclohexanone with deuterium catalyzed by platinum metals

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Abstract

2-Methyl and 2-ethyl derivatives of cyclohexanone were allowed to react with deuterium in t-BuOD using platinum group metals as catalysts. The product alcohols and the remaining ketone were examined by mass spectrometry. Over Ru, Os, and Ir, the simple addition of two deuterium atoms to the carbonyl linkage was predominant, accompanied by little isotopic exchange. Over Pt, however, isotopic exchange was significant and over Rh and Pd quite extensive. The samples obtained over Rh and Pd were further analyzed by NMR spectroscopy to determine the loci of the incorporated deuterium atoms. Deuterium exchange over Pd was almost entirely confined to the C(2) and C(6) positions, while that over Rh was smeared beyond these positions. These results can be accounted for by assuming the intermediacy of ..pi..-absorbed ..pi..-oxaallylic species on Pd and of ..beta..-diadsorbed species on Rh.

Authors:

Teratani, S ^[1]; Tanaka, K; Ogawa, H; Taya, K

Inst. of Physical and Chemical Research, Waco, Saitama, Japan

Publication Date:: Sat Aug 01 00:00:00 EDT 1981

OSTI Identifier:: 6004123

Resource Type:: Journal Article

Journal Name:: J. Catal.; (United States)

Additional Journal Information:: Journal Volume: 70:2

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; CYCLOHEXANONE; CHEMICAL REACTIONS; DEUTERIUM; ISOTOPIC EXCHANGE; DEUTERIUM COMPOUNDS; IRIDIUM; CATALYTIC EFFECTS; COMPARATIVE EVALUATIONS; OSMIUM; PLATINUM; RUTHENIUM; ALCOHOLS; CYCLOHEXANOL; KETONES; MASS SPECTROSCOPY; NMR SPECTRA; ELEMENTS; HYDROGEN COMPOUNDS; HYDROGEN ISOTOPES; HYDROXY COMPOUNDS; ISOTOPES; LIGHT NUCLEI; METALS; NUCLEI; ODD-ODD NUCLEI; ORGANIC COMPOUNDS; PLATINUM METALS; REFRACTORY METALS; SPECTRA; SPECTROSCOPY; STABLE ISOTOPES; TRANSITION ELEMENTS; 400303* - Organic Chemistry- Isotope Exchange & Isotope Separation- (-1987)

Citation Formats


                    Teratani, S, Tanaka, K, Ogawa, H, and Taya, K. Substituent effects in heterogeneous catalysis. VIII. Reactions of 2-methyl- and 2-ethylcyclohexanone with deuterium catalyzed by platinum metals.  United States: N. p., 1981. 
        Web.  doi:10.1016/0021-9517(81)90346-8.

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                    Teratani, S, Tanaka, K, Ogawa, H, & Taya, K. Substituent effects in heterogeneous catalysis. VIII. Reactions of 2-methyl- and 2-ethylcyclohexanone with deuterium catalyzed by platinum metals.  United States.  https://doi.org/10.1016/0021-9517(81)90346-8

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                    Teratani, S, Tanaka, K, Ogawa, H, and Taya, K. 1981.  
        "Substituent effects in heterogeneous catalysis. VIII. Reactions of 2-methyl- and 2-ethylcyclohexanone with deuterium catalyzed by platinum metals".  United States.  https://doi.org/10.1016/0021-9517(81)90346-8.

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@article{osti_6004123,

  title        = {Substituent effects in heterogeneous catalysis. VIII. Reactions of 2-methyl- and 2-ethylcyclohexanone with deuterium catalyzed by platinum metals},

  author       = {Teratani, S and Tanaka, K and Ogawa, H and Taya, K},

  abstractNote = {2-Methyl and 2-ethyl derivatives of cyclohexanone were allowed to react with deuterium in t-BuOD using platinum group metals as catalysts. The product alcohols and the remaining ketone were examined by mass spectrometry. Over Ru, Os, and Ir, the simple addition of two deuterium atoms to the carbonyl linkage was predominant, accompanied by little isotopic exchange. Over Pt, however, isotopic exchange was significant and over Rh and Pd quite extensive. The samples obtained over Rh and Pd were further analyzed by NMR spectroscopy to determine the loci of the incorporated deuterium atoms. Deuterium exchange over Pd was almost entirely confined to the C(2) and C(6) positions, while that over Rh was smeared beyond these positions. These results can be accounted for by assuming the intermediacy of ..pi..-absorbed ..pi..-oxaallylic species on Pd and of ..beta..-diadsorbed species on Rh.},

  doi          = {10.1016/0021-9517(81)90346-8},

  url          = {https://www.osti.gov/biblio/6004123},
  journal      = {J. Catal.; (United States)},
number       = ,

  volume       = 70:2,

  place        = {United States},

  year         = {Sat Aug 01 00:00:00 EDT 1981},

  month        = {Sat Aug 01 00:00:00 EDT 1981}

}

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