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Studies of Memory of Chirality in Amide Radical Cyclizations

SASMAL, ANIRUDDHA Studies of Memory of Chirality in Amide Radical Cyclizations. Master's Thesis, University of Pittsburgh.

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    Abstract

    Radical cyclization of amide substrates was performed to establish the Memory of Chirality (MOC). Amides with N-tert-butyl substituent due to their hindered rotation around C-N bond gives cyclized product with retention of configuration upon radical reaction condition. Chiral GC analysis and theoretical optical rotation calculation were used to verify the MOC. An unexpected 1,4-phenyl radical migration was also observed during the radical reaction of N-benzyl substituted amides.

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    Details

    Item Type: University of Pittsburgh ETD
    ETD Committee:
    ETD Committee TypeCommittee MemberEmail
    Thesis AdvisorCurran, Denniscurran@pitt.edu
    Committee MemberFloreancig, Paulflorean@pitt.edu
    Committee MemberWilcox, Craigdaylite@pitt.edu
    Title: Studies of Memory of Chirality in Amide Radical Cyclizations
    Status: Published
    Abstract: Radical cyclization of amide substrates was performed to establish the Memory of Chirality (MOC). Amides with N-tert-butyl substituent due to their hindered rotation around C-N bond gives cyclized product with retention of configuration upon radical reaction condition. Chiral GC analysis and theoretical optical rotation calculation were used to verify the MOC. An unexpected 1,4-phenyl radical migration was also observed during the radical reaction of N-benzyl substituted amides.
    Defense Date: 14 March 2011
    Approval Date: 18 January 2012
    Submission Date: 06 December 2011
    Release Date: 18 January 2012
    Access Restriction: 1 year -- Restrict access to University of Pittsburgh for a period of 1 year.
    Patent pending: No
    Number of Pages: 76
    Institution: University of Pittsburgh
    Thesis Type: Master's Thesis
    Refereed: Yes
    Degree: MS - Master of Science
    Uncontrolled Keywords: Memory of Chirality, N-tert-butyl substituted amide, 1,4-Phenyl migration
    Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
    Date Deposited: 18 Jan 2012 16:30
    Last Modified: 18 Jan 2013 01:15

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