Protecting Triazabutadienes To Afford Acid Resistance.
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.
Department of Chemistry and Biochemistry, University of Arizona, Building 41, Room 104, 1306 E University Boulevard, Tucson, AZ, 85721, USA.
Lindsay E
LE
Guzman
Department of Chemistry and Biochemistry, University of Arizona, Building 41, Room 104, 1306 E University Boulevard, Tucson, AZ, 85721, USA.
Flora W
FW
Kimani
Department of Chemistry and Biochemistry, University of Arizona, Building 41, Room 104, 1306 E University Boulevard, Tucson, AZ, 85721, USA.
John C
0000-0001-5822-4080
JC
Jewett
D000143:Acids / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry
D000143:Acids; D002070:Butadienes; D010455:Peptides
acid/base chemistry; aryl diazonium ion; hydrolysis; protecting groups; solid-phase synthesis
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