THREE STUDIES OF 2-PYRIDONE PHOTOADDUCT REACTIVITY

2-Pyridones such as iii undergo efficient [4+4] photocycloaddition reactions, yielding strained tricyclic cyclooctadiene structures iv and v, with functionality at every carbon. As part of a program to develop the chemistry of these complex adducts, three studies have been conducted. Halogenation of trans iv give rearranged i. Cope rearrangement of cis v gives vi which can undergo retro-Mannich reaction to yield unsymmtrically coupled piperidines vii. Pyridones can also undergo photo-[4+4] reactions with furans. Cycloaddition of viii yields ix. Transannular closure of ix produces triquinane x, a model system for total synthesis of crinipellin A xi.

Grantor dc:publisher

Temple University. Libraries

Year dc:date.issued

2010

Author dc:creator

• Chen, Peiling

Advisor dc:contributor.advisor

• Sieburth, Scott McNeill

Committee members dc:contributor.committeemember

• Davis, Franklin A.
• Krow, Grant

• Chemistry, Organic

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• IN COPYRIGHT- This Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available.

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Language dc:language.iso

eng

Dc Identifier Other

864884786

OAI identifier oai:identifier

oai:scholarshare.temple.edu:20.500.12613/950