Assessing the feasibility of a one-pot, tandem olefin metathesis and isomerization sequence to synthesize conjugated aromatic olefins

Author

Ajay D. Makwana, University of Tennessee at ChattanoogaFollow

Project Director

Knight, Kyle S.

Department Examiner

Lee, John P.; Park, Han J.; Giles, David

Department

Dept. of Chemistry

Publisher

University of Tennessee at Chattanooga

Place of Publication

Chattanooga (Tenn.)

Abstract

The synthesis of substituted phenylpropene dimers using a one-pot, tandem olefin metathesis and isomerization sequence has been studied. This sequence relies on the facilitated, in-situ conversion of a ruthenium carbene species (Ru=C) to a ruthenium hydride species (Ru-H) upon addition of an inorganic hydride source. Three separate reactions occur within one reaction flask: 1) olefin metathesis of the starting phenylpropene to yield phenylpropene dimer via Ru=C catalyst, 2) conversion of Ru=C to Ru-H via addition of an inorganic hydride source, 3) isomerization of phenylpropene dimer via insertion and β-hydride elimination to yield conjugated product. The focus of the study has been to determine optimal reaction conditions to facilitate the formation of a high yield of dimerized product. Thus far, the isolation of the dimerized product has been elusive due to the thermodynamically favorable formation of the isomerized dimer product. The isomerized dimer has been observed to undergo further olefin metathesis via the action of residual Ru=C catalyst resulting in the formation of several metathesis alkene products. A variety of metathesis products in the crude reaction mixture has been consistently detected via 1H NMR spectroscopy under a range of experimental conditions.

Acknowledgments

National Science Foundation The University of Tennessee at Chattanooga Department of Chemistry and Physics Grote Fund The University of Tennessee at Chattanooga Provost Student Research Award Materia, Inc.

Degree

B. S.; An honors thesis submitted to the faculty of the University of Tennessee at Chattanooga in partial fulfillment of the requirements of the degree of Bachelor of Science.

Date

8-2016

Subject

Alkenes -- Analysis

Keyword

Olefin; Tandem; Metathesis; Isomerization; Grubbs; Hydride

Discipline

Chemistry

Document Type

Theses

Extent

48 leaves

DCMI Type

Text

Language

English

Rights

http://rightsstatements.org/vocab/InC/1.0/

License

http://creativecommons.org/licenses/by-nc-nd/3.0/

Date Available

4-22-2017

Recommended Citation

Makwana, Ajay D., "Assessing the feasibility of a one-pot, tandem olefin metathesis and isomerization sequence to synthesize conjugated aromatic olefins" (2016). Honors Theses.
https://scholar.utc.edu/honors-theses/63