Investigation of new synthetic reactions: the synthesis of hydrazines via the Aza-Lossen rearrangement, the synthesis of carbamoyl azides from amines, and deprotection reactions using water at elevated temperatures

This thesis explores three rare synthetic routes: the synthesis of hydrazines via the aza-Lossen rearrangement, the synthesis of carbamoyl azides from amines, and deprotection reactions using water at elevated temperatures. The aza-Lossen reaction was found to be ideal at “infinite dilution” conditi...

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Bibliographic Details
Main Author: Mojica, Mike
Other Authors: Eckert, Charles A.
Format: Others
Language:en_US
Published: Georgia Institute of Technology 2014
Subjects:
Online Access:http://hdl.handle.net/1853/51791
Description
Summary:This thesis explores three rare synthetic routes: the synthesis of hydrazines via the aza-Lossen rearrangement, the synthesis of carbamoyl azides from amines, and deprotection reactions using water at elevated temperatures. The aza-Lossen reaction was found to be ideal at “infinite dilution” conditions and could be performed with both aryl and alkyl example. Carbamoyl azides could be synthesized in high yields from both aryl and alkyl amines. The carbamoyl azide reaction was found to be much more efficient with Cs (+1) present. Lastly, water at elevated temperatures conditions was efficient at removing various amine and hydroxyl protecting groups.