Please use this identifier to cite or link to this item:
http://hdl.handle.net/11375/11997
Title: | The Reaction of Diazoalkanes with Heterocumulenes. Mechanism and Synthetic Utility |
Authors: | Fulton, Barbara Janet |
Advisor: | Warkentin, J. |
Department: | Chemistry |
Keywords: | Chemistry;Chemistry |
Publication Date: | Oct-1978 |
Abstract: | <p>A new approach to the synthesis of 3,3-dialkyloxindole systems which involves reaction of a dialkyldiazomethane, generated (in situ) by the thermolysis of a 5,5-dialkyl-∆³-1,3,4-oxadiazolin-2-one, with an aryl isocyanate, has been developed. Minor products of the reaction are a 2-imino-5,5-dialkyl-4-oxazolidone and a 5,5-dialkylhydantoin. The synthesis of both a 2-imino-5,5-dialkyl-4-thiazolinethione and a 5,5-dialkyl-2,4-dithiohydantoin has been achieved in a similar manner, using phenyl isothiocyanate in place of phenylisocyanate. Spectroscopic data, in particular ¹³C chemical shifts, and chemical transformations are cited in support of the structural assignments. Possible mechanisms for the formation of the heterocyclic compounds are considered.</p> |
URI: | http://hdl.handle.net/11375/11997 |
Identifier: | opendissertations/692 1907 1086696 |
Appears in Collections: | Open Access Dissertations and Theses |
Files in This Item:
File | Size | Format | |
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fulltext.pdf | 4.47 MB | Adobe PDF | View/Open |
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