Ketene dimethyl thioacetal monosulfoxide was prepared in 68% overall yield in two steps starting from methylmagnesium chloride. The yield of dithioacetic acid was improved significantly by employing tetrahydrofuran as solvent and using elevated temperatures. A one-pot synthesis of ketene thioacetals from alkyl halides was developed and several ketene thioacetals were prepared by this method. Direct oxidation of ketene thioacetals using m-chloroperoxybenzoic acid provided a general route to ketene thioacetal monosulfoxides. In cases where E and Z isomeric ketene thioacetal monosulfoxides were possible, the E/Z isomeric ratio increased as the substituents on the ketene double bond was increased in size.
| Identifer | oai:union.ndltd.org:unt.edu/info:ark/67531/metadc331154 |
| Date | 08 1900 |
| Creators | Kaya, Riza |
| Contributors | Beller, Nicholas R., Brady, William Thomas, Daugherty, Kenneth E., Norton, S. J. |
| Publisher | North Texas State University |
| Source Sets | University of North Texas |
| Language | English |
| Detected Language | English |
| Type | Thesis or Dissertation |
| Format | v, 148 leaves, ill., Text |
| Rights | Public, Kaya, Riza, Copyright, Copyright is held by the author, unless otherwise noted. All rights reserved. |
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