eprintid: 7705
rev_number: 5
userid: 6
dir: disk0/00/00/77/05
datestamp: 2011-11-10 19:42:56
lastmod: 2016-11-15 13:42:50
status_changed: 2011-11-10 19:42:56
type: thesis_degree
metadata_visibility: show
contact_email: tiffany_turner@baylor.edu
item_issues_count: 0
eprint_status: archive
creators_name: Turner, Tiffany Renee
creators_email: tiffany_turner@baylor.edu
title: 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
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: public
keywords: acyl radical fragmentation; hydrindanones; radical cyclization
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.
date: 2006-06-29
date_type: completed
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Curran, Dennis P
etdcommittee_name: Brummond, Kay
etdcommittee_name: Wipf, Peter
etdcommittee_email: curran@pitt.edu
etdcommittee_email: kbrummon@pitt.edu
etdcommittee_email: pwipf@pitt.edu
etdcommittee_id: CURRAN
etdcommittee_id: KBRUMMON
etdcommittee_id: PWIPF
etd_defense_date: 2005-07-01
etd_approval_date: 2006-06-29
etd_submission_date: 2006-04-28
etd_access_restriction: immediate
etd_patent_pending: FALSE
assigned_doi: doi:10.5195/pitt.etd.2011.7705
thesis_type: thesis
degree: MS
committee: Dennis P. Curran (curran@pitt.edu) - Committee Chair
committee: Kay Brummond (kbrummon@pitt.edu) - Committee Member
committee: Peter Wipf (pwipf@pitt.edu) - Committee Member
etdurn: etd-04282006-010411
other_id: http://etd.library.pitt.edu/ETD/available/etd-04282006-010411/
other_id: etd-04282006-010411
citation:   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)  
document_url: http://d-scholarship-dev.library.pitt.edu/7705/1/turnertiffanyr2006.pdf