ic8b02129_si_001.pdf (1.91 MB)
Trimethylsilyl-Induced N–O Bond Cleavage in Nitrous Oxide-Derived Aminodiazotates
journal contribution
posted on 2018-09-14, 00:00 authored by Yizhu Liu, Léonard
Y. M. Eymann, Euro Solari, Farzaneh Fadaei Tirani, Rosario Scopelliti, Kay SeverinThe
chemical activation of nitrous oxide (N2O) typically
results in O-atom transfer and the extrusion of N2 gas.
In contrast, reactions of N-trimethylsilyl (TMS)-substituted
amides with N2O give inorganic or organic azides, with
concomitant formation of silanols or siloxanes. N-TMS-substituted amides are also able to induce N–O bond cleavage
in N2O-derived dialkylaminodiazotates, generating tetrazene
salts. These results indicate the potential of silyl groups in devising
transformations, in which N2O acts as an N-atom donor.
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N 2 O actsN-atom donorTMS-substituted amidesazideNitrous Oxide-Derived AminodiazotatesbondN 2 gastransformationcontrastsiloxanecleavageformationtrimethylsilylCleavagetetrazene saltsBondextrusionN 2 ON 2 O-derived dialkylaminodiazotatesO-atom transferoxideTrimethylsilyl-Inducedsilyl groupschemical activationsilanol
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