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Stereochemical and Reactivity Studies of ETIC/Enol Ether Cleavage Reactions

Smotryski, Jennifer (2007) Stereochemical and Reactivity Studies of ETIC/Enol Ether Cleavage Reactions. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

The electron transfer initiated cyclization (ETIC)/enol ether cleavage reaction has been developed in the Floreancig group as a mild and selective method for the formation of substituted tetrahydropyran rings systems, which are common in natural products. Reactions untilizing the initial substrate result in a methyl ketone substituted tetrahydropyran ring, however the addition of a side chain along the alkyl backbone of the substrate can lead to di-substituted tetrahydropyran rings. Products with side chains in the alpha and gamma positions containing aliphatic, alkoxy and siloxy groups have been synthesized. The cis/trans stereochemistry of the two side chains has been predicted based on transition state models and has been verified by NMR experimentation.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Smotryski, Jenniferseolena22@hotmail.com
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairFloreancig, Paul Eflorean@pitt.eduFLOREAN
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Committee MemberBrummond, Kay Mkbrummon@pitt.eduKBRUMMON
Date: 23 January 2007
Date Type: Completion
Defense Date: 9 November 2006
Approval Date: 23 January 2007
Submission Date: 14 November 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: Electron Transfer Initiated Cyclization; enol ether cleavage; Photoinitiated electron transfer
Other ID: http://etd.library.pitt.edu/ETD/available/etd-11142006-113437/, etd-11142006-113437
Date Deposited: 10 Nov 2011 20:04
Last Modified: 15 Nov 2016 13:51
URI: http://d-scholarship.pitt.edu/id/eprint/9665

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