eprintid: 9665
rev_number: 4
userid: 6
dir: disk0/00/00/96/65
datestamp: 2011-11-10 20:04:50
lastmod: 2016-11-15 13:51:34
status_changed: 2011-11-10 20:04:50
type: thesis_degree
metadata_visibility: show
contact_email: seolena22@hotmail.com
item_issues_count: 0
eprint_status: archive
creators_name: Smotryski, Jennifer
creators_email: seolena22@hotmail.com
title: Stereochemical and Reactivity Studies of ETIC/Enol Ether Cleavage Reactions
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: public
keywords: Electron Transfer Initiated Cyclization; enol ether cleavage; Photoinitiated electron transfer
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.
date: 2007-01-23
date_type: completed
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Floreancig, Paul E
etdcommittee_name: Wilcox, Craig
etdcommittee_name: Brummond, Kay M
etdcommittee_email: florean@pitt.edu
etdcommittee_email: daylite@pitt.edu
etdcommittee_email: kbrummon@pitt.edu
etdcommittee_id: FLOREAN
etdcommittee_id: DAYLITE
etdcommittee_id: KBRUMMON
etd_defense_date: 2006-11-09
etd_approval_date: 2007-01-23
etd_submission_date: 2006-11-14
etd_access_restriction: immediate
etd_patent_pending: FALSE
assigned_doi: doi:10.5195/pitt.etd.2011.9665
thesis_type: thesis
degree: MS
committee: Paul E. Floreancig (florean@pitt.edu) - Committee Chair
committee: Craig Wilcox (daylite@pitt.edu) - Committee Member
committee: Kay M. Brummond (kbrummon@pitt.edu) - Committee Member
etdurn: etd-11142006-113437
other_id: http://etd.library.pitt.edu/ETD/available/etd-11142006-113437/
other_id: etd-11142006-113437
citation:   Smotryski, Jennifer  (2007) Stereochemical and Reactivity Studies of ETIC/Enol Ether Cleavage Reactions.  Master's Thesis, University of Pittsburgh.    (Unpublished)  
document_url: http://d-scholarship-dev.library.pitt.edu/9665/1/finalthesis.pdf