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Chemoselective nitration of phenols with tert-butyl nitrite in solution and on solid support.

ABSTRACT: tert-Butyl nitrite was identified as a safe and chemoselective nitrating agent that provides preferentially mononitro derivatives of phenolic substrates in the presence of potentially competitive functional groups. On the basis of our control experiments, we propose that the reaction proceeds through the formation of O-nitrosyl intermediates prior to C-nitration via homolysis and oxidation. The reported nitration method is compatible with tyrosine-containing peptides on solid support in the synthesis of fluorogenic substrates for characterization of proteases.

SUBMITTER: Koley D

PROVIDER: S-EPMC2758266 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Chemoselective nitration of phenols with tert-butyl nitrite in solution and on solid support.

Koley Dipankar D Colón Olvia C OC Savinov Sergey N SN

Organic letters 20090901 18

tert-Butyl nitrite was identified as a safe and chemoselective nitrating agent that provides preferentially mononitro derivatives of phenolic substrates in the presence of potentially competitive functional groups. On the basis of our control experiments, we propose that the reaction proceeds through the formation of O-nitrosyl intermediates prior to C-nitration via homolysis and oxidation. The reported nitration method is compatible with tyrosine-containing peptides on solid support in the synt ...[more]

PMID: 19697919

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