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Protecting Triazabutadienes To Afford Acid Resistance
Lindsay E Guzman1, Flora W Kimani1, John C Jewett1
1Department of Chemistry and Biochemistry, University of Arizona, Building 41, Room 104, 1306 E University Boulevard, Tucson, AZ, 85721, USA.
Abstract:
Recent work on triazabutadienes has shown that they have the ability to release aryl diazonium ions under exceptionally mild acidic conditions. There are instances that require that this release be prevented or minimized. Accordingly, a base-labile protection strategy for the triazabutadiene is presented. It affords enhanced synthetic and practical utility of the triazabutadiene. The effects of steric and electronic factors in the rate of removal are discussed, and the triazabutadiene protection is shown to be compatible with the traditional acid-labile protection strategy used in solid phase peptide synthesis.
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