Phosphorous containing small cycles are very important building blocks in organic
and medicinal chemistry. Many of their derivatives, especially cyclopropyl- and 1,2-
epoxypropylphosphonates, have attracted great attention due to the broad spectrum
of their biological properties including antiviral, anticancer, antibiotic, antibacterial,
pesticidal, insecticidal and enzyme inhibitory activities.
The Darzens condensation is one of the most potential methodologies for the
preperation of & / #945 / ,& / #946 / -epoxy carbonyl compounds with complete control of two
stereogenic centers. The Darzens condensation reaction represents one of the
classical C-C and C-O bond-forming processes.
In the first part of the thesis, reactions of a broad range of acyl phosphonates with
substituted & / #945 / -bromo acetophenones at room temperature in the presence of different
bases were examined in order to illustrate the reaction and the substituent effect on
the reaction. The reaction affords two diastereomeric epoxy phosphonates in good
yields and high diastereoselectivities.
In the second part of the thesis, it is shown that a variety of radicals can be generated
from the substituted aryl boronic acids with Mn(OAc)3. In the presence of
acetonitrile, these radicals were added to carbon of acetonitrile to afford the
corresponding ketones after hydrolysis of the formed imine with moderate to good
yields.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/2/12610199/index.pdf |
| Date | 01 November 2008 |
| Creators | Pirkin, Eser |
| Contributors | Demir, Ayhan Sitki |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | M.S. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for METU campus |
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