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Studies of Memory of Chirality in Amide Radical Cyclizations

SASMAL, ANIRUDDHA (2012) Studies of Memory of Chirality in Amide Radical Cyclizations. Master's Thesis, University of Pittsburgh. (Unpublished)

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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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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
SASMAL, ANIRUDDHAans142@pitt.eduANS142
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Thesis AdvisorCurran, Denniscurran@pitt.eduCURRAN
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Date: 18 January 2012
Date Type: Publication
Defense Date: 14 March 2011
Approval Date: 18 January 2012
Submission Date: 6 December 2011
Access Restriction: 1 year -- Restrict access to University of Pittsburgh for a period of 1 year.
Number of Pages: 76
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: Memory of Chirality, N-tert-butyl substituted amide, 1,4-Phenyl migration
Date Deposited: 18 Jan 2012 21:30
Last Modified: 15 Nov 2016 13:55


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