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Beak, Peter Lutz, Gary Paul 2011-05-07T14:27:28Z 2011-05-07T14:27:28Z 10000-01-01 1991 An investigation of the diastereoselective $\beta$-metalation and of the structure of a carbanion of a $\beta$-phenyl tertiary amide has been carried out. The directed metalation has been found to occur with high diastereoselectivity and the resulting carbanion is best described as a pyramidal benzyllithium species based on $\sp{13}$C NMR evidence. Secondary amides have been shown to act as directing groups for $\beta$-lithiations, and the dianion homoenolate equivalents have been shown to react with a variety of electrophiles. We have found that the remote metalations can be directed by secondary amides employing several anion stabilizing groups, and the secondary amides can undergo remote metalations when no $\alpha$-alkyl substituent is present. The rate of the directed deprotonation has been found to be dependent upon the chain length between the amide group and the anion stabilizing group. The investigation of using secondary amides as homoenolate equivalents as well as the potential and limitations of these homoenolate equivalents will be addressed. Made available in DSpace on 2011-05-07T14:27:28Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9210904.pdf: 8408626 bytes, checksum: b9b02a952dbce7f58d21b8f39679d925 (MD5) Previous issue date: 1991 Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T15:06:55Z Item is restricted indefinitely. Restriction data tranferred 2014-07-01T11:32:09-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission ETDs are only available to UIUC Users without author permission U of I Only AAI9210904 (UMI)AAI9210904 http://hdl.handle.net/2142/23798 eng Copyright 1991 Lutz, Gary Paul Chemistry, Organic Beta-lithiations of carboxamides: An investigation of the regio- and stereoselectivity of directed lithiations text Chemistry, Organic Chemistry, Organic University of Illinois at Urbana-Champaign Dissertation Ph.D.