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Protecting Triazabutadienes To Afford Acid Resistance.


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.

SUBMITTER: Guzman LE 

PROVIDER: S-EPMC5170869 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Protecting Triazabutadienes To Afford Acid Resistance.

Guzman Lindsay E LE   Kimani Flora W FW   Jewett John C JC  

Chembiochem : a European journal of chemical biology 20161021 23


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  ...[more]

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