Davis, Matthew M
(2009)
The Rh(I)-Catalyzed Cyclocarbonylation of Allenol Esters to Prepare α-Acetoxy 4-Alkylidene Cyclopent-3-en-2-ones.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
The Rh(I)-catalyzed allenic cyclocarbonylation reaction is an effective method for forming 4-alkylidene cyclopentenones. The scope of this methodology was expanded to include the cyclocarbonylation of allenol acetates to provide α-acetoxy-4-alkylidene cyclopentenones. The diastereoselectivity of the [3,3]-sigmatropic rearrangement to form the allenol acetates and cyclocarbonylation reaction were examined. During the course of the Rh(I)-catalyzed cyclocarbonylation reaction two rhodium metallocycle intermediates were observed and structures are postulated based upon 1H and 13C NMR data. Liberation of the acetate to the free alcohol was also accomplished yielding α-hydroxy-4-alkylidene cyclopentenones.
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Details
Item Type: |
University of Pittsburgh ETD
|
Status: |
Unpublished |
Creators/Authors: |
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ETD Committee: |
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Date: |
29 September 2009 |
Date Type: |
Completion |
Defense Date: |
15 July 2009 |
Approval Date: |
29 September 2009 |
Submission Date: |
14 August 2009 |
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: |
alkyne; allene; cyclocarbonylation; cyclopentenone; metallocycle; rhodium |
Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-08142009-114302/, etd-08142009-114302 |
Date Deposited: |
10 Nov 2011 19:59 |
Last Modified: |
15 Nov 2016 13:49 |
URI: |
http://d-scholarship.pitt.edu/id/eprint/9096 |
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