Synthetic and Mechanistic Investigation of Alpha-Amido Carbanions

The removal of an sp('3) proton from a carbon adjacent to nitrogen followed by reaction with an electrophile to effect substitution at that site provides umpolung of the customary amine polarity. This thesis reports the use of a carbonyl moiety to aid in the stabilization of negative charge adjacent to nitrogen. The syntheses of ten different N,N-dialkyl amide systems are reported, five of which have been successfully substituted via an (alpha)-amido carbanionic intermediate.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Zajdel, William John

• Chemistry, Organic

Identifier

(UMI)AAI8303035

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70208