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SIGMATROPIC REARRANGEMENTS OF DIVINYLCYCLOPROPANES AND CYCLIZATIONS INVOLVING β-ELIMINATION OF SULFONYL RADICALS

Hay, Everett Ben (2014) SIGMATROPIC REARRANGEMENTS OF DIVINYLCYCLOPROPANES AND CYCLIZATIONS INVOLVING β-ELIMINATION OF SULFONYL RADICALS. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

The first chapter of this dissertation describes the synthesis and reactions of a family of 1,1-divinylcyclopropanes, including the discovery and studies of several sigmatropic rearrangement cascades. Also discussed is the radical [3+2] cyclization of 1,1-divinylcyclopropanes with the potential for memory of chirality.
The second chapter deals with the elimination of sulfonyl radicals during radical cyclizations of ene-sulfonamides. A family of polycyclic imines and a family of oxindole products were synthesized from polycyclic ene-sulfonamide precursors.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Hay, Everett Benhay.eben@gmail.com
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Committee MemberWilcox, Craig Sdaylite@pitt.eduDAYLITE
Committee MemberSmithgall, Thomas Etsmithga@pitt.eduTSMITHGA
Date: 18 September 2014
Date Type: Publication
Defense Date: 15 July 2014
Approval Date: 18 September 2014
Submission Date: 18 July 2014
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 164
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: Cyclopropane, Sigmatropic Rearrangement, Radical Cyclization, Sulfonyl Radical
Date Deposited: 18 Sep 2014 16:39
Last Modified: 15 Nov 2016 14:22
URI: http://d-scholarship.pitt.edu/id/eprint/22382

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