The objective of this study was to develop new synthetical routes to natural and industrial products utilizing ketene cycioaddition reactions. The cycioaddition of diphenylketene with α,β-unsaturated imines yields (2+2) cycioaddition products, g-lactams. However, electron donating groups, such as dimethylamine, in the 4-position of the α,β-unsaturated imines result in (4+2) cycloaddition products, ∂-lactams. Dichloroketene reacted with α,β-unsaturated imines to yield (4+2) cycloaddition products, g-lactams. Large substituents in the 4-position of a, ^-unsaturated imines resulted in a (2+2) cycioaddition product, β-lactam. The ∂-lactams derived from dichloroketene are easily dehydrochlorinated to the corresponding 2-pyridornes.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc330680 |
| Date | 08 1900 |
| Creators | Shieh, Chia Hui |
| Contributors | Brady, William Thomas, Schwartz, Martin, Norton, S. J., Jones, Paul R. |
| Publisher | North Texas State University |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | iv, 86 leaves : ill., Text |
| Rights | Public, Shieh, Chia Hui, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved. |
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