Alkane Metathesis Schrock

Olefin metathesis, or alkene metathesis, is an important process in petroleum refining and in the synthesis of important compounds such as pharmaceuticals.

The mechanism of olefin metathesis is related to pericyclic reactions like Diels Alder and [2 2] reactions.

In larger scale, industrial reactions, air- and moisture-sensitivity is usually a less compelling factor than speed. D., College of Saint Benedict / Saint John's University (with contributions from other authors as noted).

In addition to the simple "partner-swapping" of olefin metathesis, which is very important to the petroelum industry, there are other useful variations on the reaction.

In particular, terminal olefins (with the double bond at the end of the chain) are converted into internal olefins (with the double bond somewhere in the middle of the chain). The surface of the metal oxides may be covered with a mixture of hydroxyl groups as well as terminal oxides (M=O groups).

The terminal oxides on the surface are the important part of the catalyst.

A variety of catalysts have been developed for olefin metathesis.

The laboratories of Bob Grubbs at Cal Tech and Dick Schrock at MIT have been particularly important in this area, although other labs have contributed significantly, including that of Amir Hoveyda at Boston College.

The reaction, it turns out, involves a [2 2] cycloaddition of an alkene to a metal alkylidene (to the metal-carbon double bond).

This reaction results in a four-membered ring, called a metallacyclobutane.

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  • Alkane Metathesis by Tandem Alkane
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    This Account describes systems that we have developed for alkane metathesis based on the tandem operation of catalysts for alkane dehydrogenation and olefin metathesis. As dehydrogenation catalysts, we used pincer-ligated iridium complexes, and we initially investigated Schrock-type Mo or W alkylidene complexes as olefin metathesis catalysts. The interoperability of the catalysts typically.…

  • Olefin Metathesis in Organic Synthesis - Princeton University
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    Olefin Metathesis in Organic Synthesis Wendy Jen MacMillan Group Meeting January 17, 2001 I. Well-defined alkene metathesis catalysts II. Applications of Olefin Metathesis…

  • Research The Schrock Group
    Reply

    This research involves the application of metathesis reactions in organic chemistry. Most recently the research has focussed on reactions that produce as high as 99% Z products in good yields. Examples include Z -selective coupling of terminal olefins, ethenolysis, cross-metathesis, ring-closing, or alkane metathesis reactions.…

  • Alkane metathesis schrock Alkane metathesis by
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    Alkane Metathesis. Alkane metathesis by tandem alkane-dehydrogenation-olefin "a series of well-defined metathesis catalysts–synthesis of rucl2chr′pr32 and its reactions".-metathesis is synthetically equivalent to and has replaced a procedure of ozonolysis of an alkene to two ketone fragments followed by the reaction of one of them.…

  • ALKANE METATHESIS AND RELATED REACTIONS
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    ALKANE METATHESIS AND RELATED REACTIONS Reported by Yang Wang April 7, 2011 INTRODUCTION Alkanes are the major constituents of petroleum and the most important components of…

  • Metathesis of Alkanes and Related Reactions -
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    Alkane metathesis is a novel catalytic and direct transformation of two molecules of a given alkane into its lower and higher homologues; moreover, the process proceeds at relatively low temperature ambient conditions or higher.…

  • Richard Schrock - ResearchGate
    Reply

    Olefin metathesis has had a large impact on modern organic chemistry, but important shortcomings remain for example, the lack of efficient processes that can be used to generate acyclic alkenyl.…

  • Evaluation of Molybdenum and Tungsten Metathesis Catalysts.
    Reply

    Evaluation of Molybdenum and Tungsten Metathesis Catalysts for Homogeneous Tandem Alkane Metathesis Brad C. Bailey,† Richard R. Schrock,*,† Sabuj Kundu, ‡Alan S. Goldman, Zheng Huang,§…

  • Alkane metathesis - Wikipedia
    Reply

    Alkane metathesis is a class of chemical reaction in which an alkane is rearranged to give a longer or shorter alkane product. It is similar to olefin metathesis, except that olefin metathesis cleaves and recreates a carbon-carbon double bond, but alkane methathesis operates on a…

  • Olefin metathesis - Wikipedia
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    Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes olefins by the scission and regeneration of carbon-carbon double bonds.…

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