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Conversion of Methanol to 2,2,3-Trimethylbutane (Triptane) over Indium(III) Iodide

Bercaw, John E. and Diaconescu, Paula L. and Grubbs, Robert H. and Hazari, Nilay and Kay, Richard D. and Labinger, Jay A. and Mehrkhodavandi, Parisa and Morris, George E. and Sunley, Glenn J. and Vagner, Patrick (2007) Conversion of Methanol to 2,2,3-Trimethylbutane (Triptane) over Indium(III) Iodide. Inorganic Chemistry, 46 (26). pp. 11371-11380. ISSN 0020-1669. https://resolver.caltech.edu/CaltechAUTHORS:20170419-150139603

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Abstract

InI_3 is able to catalyze the conversion of methanol to a mixture of hydrocarbons at 200 °C with one highly branched alkane, 2,2,3-trimethylbutane (triptane), being obtained in high selectivity. The mechanism for InI_3-catalyzed reactions appears to be basically the same as that proposed for the previously studied ZnI_2-catalyzed system in which sequential methylation of olefins is followed by competing reactions of the resulting carbocation:  proton loss to give the next olefin vs hydride transfer to give the corresponding alkane. Although the reaction conditions and typical triptane yields achievable with ZnI_2 and InI_3 are quite similar, the two systems behave rather differently in a number of important particulars, including significant differences between the detailed product distributions. Most of the differences in behavior can be ascribed to the stronger Lewis acidity of InI_3, including the ability to activate some alkanes, the higher activity for methylation of arenes, and the fact that methanol conversion can be observed at somewhat lower temperatures with InI_3 than with ZnI_2.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ic7014447DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ic7014447PublisherArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Labinger, Jay A.0000-0002-1942-9232
Additional Information:© 2007 American Chemical Society. Received July 20, 2007. Publication Date (Web): November 30, 2007. We thank Xingwei Li for useful discussions and Eugene Zaluzec for obtaining the PIANO analysis. This work was supported by BP through the MC2 program.
Funders:
Funding AgencyGrant Number
BP MC2 ProgramUNSPECIFIED
Issue or Number:26
Record Number:CaltechAUTHORS:20170419-150139603
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170419-150139603
Official Citation:Conversion of Methanol to 2,2,3-Trimethylbutane (Triptane) over Indium(III) Iodide John E. Bercaw, Paula L. Diaconescu, Robert H. Grubbs, Nilay Hazari, Richard D. Kay, Jay A. Labinger, Parisa Mehrkhodavandi, George E. Morris, Glenn J. Sunley, and Patrick Vagner Inorganic Chemistry 2007 46 (26), 11371-11380 DOI: 10.1021/ic7014447
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76716
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:19 Apr 2017 22:33
Last Modified:03 Oct 2019 17:49

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