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The Rh(I)-Catalyzed Cyclocarbonylation of Allenol Esters to Prepare α-Acetoxy 4-Alkylidene Cyclopent-3-en-2-ones

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 (Unpublished)

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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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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Davis, Matthew Mmmd23@pitt.eduMMD23
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairBrummond, Kay Mkbrummon@pitt.eduKBRUMMON
Committee MemberCurran, Denniscurran@pitt.eduCURRAN
Committee MemberMeyer, Taratmeyer@pitt.eduTMEYER
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:, etd-08142009-114302
Date Deposited: 10 Nov 2011 19:59
Last Modified: 15 Nov 2016 13:49


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