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Concentration Studies on the Radical Cyclizations of Enol acetates and Enol carbonates and the Possible Formation of 4-Hydrindanones via an Uncommon Acyl Radical Fragmentation

Turner, Tiffany Renee (2006) Concentration Studies on the Radical Cyclizations of Enol acetates and Enol carbonates and the Possible Formation of 4-Hydrindanones via an Uncommon Acyl Radical Fragmentation. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

Recently, Uta Wille and coworkers proposed a novel non-chain, self-terminating, oxidative radical cyclization that ends with the uncommon homolytic cleavage of an acyl-oxygen bond to give a ketone and an acyl radical (J. Amer. Chem. Soc. 2002, 124 (1), 14-15). We present the results of our study into this type of unusual radical fragmentation. Our focus was on initiating radical intermediates 53a,b thru thermal means using Bu3SnH to produce ketone 54 as opposed to photo-induced methods used by Wille. In our work, we were unable to produce 54 in sufficient yields, but we were able to isolate carbonyl compounds 62-63α,β. Based on these results, we cannot rule out an alternative polar fragmentation.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Turner, Tiffany Reneetiffany_turner@baylor.edu
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberBrummond, Kaykbrummon@pitt.eduKBRUMMON
Committee MemberWipf, Peterpwipf@pitt.eduPWIPF
Date: 29 June 2006
Date Type: Completion
Defense Date: 1 July 2005
Approval Date: 29 June 2006
Submission Date: 28 April 2006
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: acyl radical fragmentation; hydrindanones; radical cyclization
Other ID: http://etd.library.pitt.edu/ETD/available/etd-04282006-010411/, etd-04282006-010411
Date Deposited: 10 Nov 2011 19:42
Last Modified: 15 Nov 2016 13:42
URI: http://d-scholarship.pitt.edu/id/eprint/7705

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