Dissertation/Thesis Abstract

Three studies of 2-pyridone photoadduct reactivity
by Chen, Peiling, Ph.D., Temple University, 2010, 520; 3390640
Abstract (Summary)

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.

Indexing (document details)
Advisor: Sieburth, Scott McN.
Commitee: Davis, Franklin A., Grant, Krow R., Winkler, Jeffrey D.
School: Temple University
Department: Chemistry
School Location: United States -- Pennsylvania
Source: DAI-B 71/02, Dissertation Abstracts International
Source Type: DISSERTATION
Subjects: Organic chemistry
Keywords: 2-pyridone, Photoadducts, Photocycloaddition
Publication Number: 3390640
ISBN: 978-1-109-60180-0
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