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

被引:14
作者
ADAMS, CM
SHARTS, CM
SHACKELFORD, SA
机构
[1] The Frank J. Seiler Research Laboratory USAF Academy Colorado Springs
关键词
ANHYDROUS NITRATION; NITRONIUM TRIFLATE; TETRABUTYLAMMONIUM NITRATE; TRIFLIC ANHYDRIDE;
D O I
10.1016/S0040-4039(00)61671-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:6669 / 6672
页数:4
相关论文
共 13 条
[1]  
ADAMS CM, 1992, 11TH ROCK MOUNT REG
[2]   THERMAL-DECOMPOSITION OF ENERGETIC MATERIALS .3. TEMPORAL BEHAVIORS OF THE RATES OF FORMATION OF THE GASEOUS PYROLYSIS PRODUCTS FROM CONDENSED-PHASE DECOMPOSITION OF 1,3,5-TRINITROHEXAHYDRO-S-TRIAZINE [J].
BEHRENS, R ;
BULUSU, S .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (22) :8877-8891
[3]   THERMAL-DECOMPOSITION OF ENERGETIC MATERIALS .2. DEUTERIUM-ISOTOPE EFFECTS AND ISOTOPIC SCRAMBLING IN CONDENSED-PHASE DECOMPOSITION OF OCTAHYDRO-1,3,5,7-TETRANITRO-1,3,5,7-TETRAZOCINE [J].
BEHRENS, R ;
BULUSU, S .
JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (15) :5838-5845
[4]   THERMAL-DECOMPOSITION OF ENERGETIC MATERIALS .4. DEUTERIUM-ISOTOPE EFFECTS AND ISOTOPIC SCRAMBLING (H/D, C-13/O-18, N-14/N-15) IN CONDENSED-PHASE DECOMPOSITION OF 1,3,5-TRINITROHEXAHYDRO-S-TRIAZINE [J].
BEHRENS, R ;
BULUSU, S .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (22) :8891-8897
[5]  
Feuer H., 1990, NITRO COMPOUNDS RECE
[6]  
KOSLOVA IK, 1981, IZU AKAD NAUK SSSR K, V11, P2563
[7]  
KOSLOVA IK, 1981, IZU AKAD NAUK SSSR K, V11, P2556
[8]   COMPARATIVE MECHANISTIC THERMOCHEMICAL DECOMPOSITION ANALYSES OF LIQUID HEXAHYDRO-1,3,5-TRINITRO-1,3,5-TRIAZINE (RDX) USING THE KINETIC DEUTERIUM-ISOTOPE EFFECT APPROACH [J].
RODGERS, SL ;
COOLIDGE, MB ;
LAUDERDALE, WJ ;
SHACKELFORD, SA .
THERMOCHIMICA ACTA, 1991, 177 :151-168
[9]  
Shackelford S. A., 1991, PROPELL EXPLOS PYROT, V16, P279
[10]  
SHACKELFORD SA, 1992, NOV PLM TNO ONR WORK