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.
|Advisor:||Sieburth, Scott McN.|
|Commitee:||Davis, Franklin A., Grant, Krow R., Winkler, Jeffrey D.|
|School Location:||United States -- Pennsylvania|
|Source:||DAI-B 71/02, Dissertation Abstracts International|
|Keywords:||2-pyridone, Photoadducts, Photocycloaddition|
Copyright in each Dissertation and Thesis is retained by the author. All Rights Reserved
The supplemental file or files you are about to download were provided to ProQuest by the author as part of a
dissertation or thesis. The supplemental files are provided "AS IS" without warranty. ProQuest is not responsible for the
content, format or impact on the supplemental file(s) on our system. in some cases, the file type may be unknown or
may be a .exe file. We recommend caution as you open such files.
Copyright of the original materials contained in the supplemental file is retained by the author and your access to the
supplemental files is subject to the ProQuest Terms and Conditions of use.
Depending on the size of the file(s) you are downloading, the system may take some time to download them. Please be