Penich, Jessie Michael
(2011)
Ruthenium-Catalyzed [3,3]-Sigmatropic Rearrangements of α-Branched Allyl Vinyl Ethers.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
Previous research carried out in our group has demonstrated the ability of the cationic ruthenium complex [CpRu(MeCN)3]PF6 in tandem with a chiral picolinamide ligand and a Lewis acid co-catalyst to facilitate the catalytic, asymmetric [3,3]-sigmatropic rearrangement of α-unbranched aromatic allyl vinyl ethers at ambient temperature. This thesis describes my efforts to a.) extend the Ru-catalyzed Claisen methodology to α-branched substrates and b.) investigate the mechanism of this class of transformation. It was determined that [CpRu(MeCN)3]PF6 in conjunction with several novel N-phenol picolinomide ligands serve as highly-active catalysts for the rearrangement of α-branched aromatic allyl vinyl ethers. Although regio- and stereoselectivity are poor at this point, reactions proceed to complete conversion at ambient temperature in as little as 2 h in CH2Cl2 with no Lewis acid or any other additives required.
Share
Citation/Export: |
|
Social Networking: |
|
Details
Item Type: |
University of Pittsburgh ETD
|
Status: |
Unpublished |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID |
---|
Penich, Jessie Michael | jmp135@pitt.edu | JMP135 | |
|
ETD Committee: |
|
Date: |
14 September 2011 |
Date Type: |
Completion |
Defense Date: |
6 May 2011 |
Approval Date: |
14 September 2011 |
Submission Date: |
19 May 2011 |
Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
Institution: |
University of Pittsburgh |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Degree: |
MS - Master of Science |
Thesis Type: |
Master's Thesis |
Refereed: |
Yes |
Uncontrolled Keywords: |
catalysis; Claisen Rearrangement; organic chemistry; transition metal; aldehyde; allylic substitution; picolinamide; metal-allyl |
Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-05192011-203620/, etd-05192011-203620 |
Date Deposited: |
10 Nov 2011 19:45 |
Last Modified: |
15 Nov 2016 13:43 |
URI: |
http://d-scholarship.pitt.edu/id/eprint/7918 |
Metrics
Monthly Views for the past 3 years
Plum Analytics
Actions (login required)
|
View Item |