The synthesis and use of cyclic nitronic esters

The Lewis acid promoted (4+2) cycloaddition of nitrostyrenes with various dienophiles was examined and several issues of selectivity were addressed. Anti diastereomers are formed exclusively in high yields in the cycloaddition with cyclic alkenes. Lewis acid complexation was examined by conducting a Hammett study which showed that electron-rich nitrostyrenes cyclize the fastest. It was shown that nitroalkenes can behave as the diene component of the cycloaddition with cyclic dienes due to the effect of the Lewis acid. Finally, the selectivity of the intramolecular cycloaddition is highly dependant upon the position of sp$\sp2$ centers in the tether. If that center is conjugated with the diene, syn diastereomers are afforded exclusively.

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

2011

Author dc:creator

• Kesler, Brenda S.

Contributors dc:contributor

• Denmark, Scott E.

• Chemistry, Organic

Statement dc:rights

• Copyright 1993 Kesler, Brenda S.

Language dc:language

eng

Identifier

AAI9329080
(UMI)AAI9329080

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/21280