ELECTROPHILIC TETRAALKYLAMMONIUM NITRATE NITRATION .1. CONVENIENT NEW ANHYDROUS NITRONIUM TRIFLATE SYNTHESIS AND IN-SITU HETEROCYCLIC N-NITRATION

Reaction of tetra-n-butylammonium nitrate and triflic anhydride, CF3SO2OSO2CF3 (Tf2O), in dichloromethane (CH2Cl2) solvent at O degrees C, produces anhydrous nitronium nitrate, NO2OSO2CF3 (NO2OTf). Subsequent introduction of various heterocycles and their N-acetylated analogs yield N-nitrated produc...

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Published inTetrahedron letters Vol. 34; no. 42; pp. 6669 - 6672
Main Authors ADAMS, CM, SHARTS, CM, SHACKELFORD, SA
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 15.10.1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONDENSED-PHASE DECOMPOSITION
ENERGETIC MATERIALS
1,3,5-TRINITROHEXAHYDRO-S-TRIAZINE
ANHYDROUS NITRATION
TRIFLIC ANHYDRIDE
NITRONIUM TRIFLATE
TETRABUTYLAMMONIUM NITRATE
THERMAL-DECOMPOSITION
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Summary:Reaction of tetra-n-butylammonium nitrate and triflic anhydride, CF3SO2OSO2CF3 (Tf2O), in dichloromethane (CH2Cl2) solvent at O degrees C, produces anhydrous nitronium nitrate, NO2OSO2CF3 (NO2OTf). Subsequent introduction of various heterocycles and their N-acetylated analogs yield N-nitrated products in 20-76% yield with an overall one-pot procedure.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)61671-4