Synthesis of pentafluorosulfanylpyrazole and pentafluorosulfanyl-1,2,3-triazole and their derivatives as energetic materials by click chemistry

被引：186
作者：
Ye, Chengfeng [1 ]
Gard, Gary L.
Winter, Rolf W.
Syvret, Robert G.
Twamley, Brendan
Shreeve, Jean'ne M.
机构：
[1] Univ Idaho, Dept Chem, Moscow, ID 83844 USA
[2] Portland State Univ, Dept Chem, Portland, OR 97207 USA
[3] Air Prod & Chem Inc, Allentown, PA 18195 USA
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 19期
关键词：
D O I：
10.1021/ol701602a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1-Pentafluorosulfanyl acetylene and its derivatives react with azide or diazomethane giving rise to an SF5-substituted 1,2,3-triazole or pyrazole. The SF5 group increases density remarkably and as a result enhances the detonation performance of the energetic materials relative to the CF3 group.
引用
收藏
页码：3841 / 3844
页数：4
相关论文
共 52 条
[1]   New and convenient method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic organic compounds [J].
Aït-Mohand, S ;
Dolbier, WR .
ORGANIC LETTERS, 2002, 4 (17) :3013-3015
[2]  
BAILEY WH, 2004, Patent No. 2004146453
[3]  
BECKE AD, 1988, PHYS REV A, V37, P785, DOI DOI 10.1103/PHYS.REV.B.37-785
[4]  
BILLEN D, 2006, Patent No. 2006134468
[5]   A new method for the synthesis of aromatic sulfurpentafluorides and studies of the stability of the sulfurpentafluoride group in common synthetic transformations [J].
Bowden, RD ;
Comina, PJ ;
Greenhall, MP ;
Kariuki, BM ;
Loveday, A ;
Philp, D .
TETRAHEDRON, 2000, 56 (21) :3399-3408
[6]   Synthesis and epoxidation of 1,3-, 1,4-, and 1,5-alkadienes with Pentafluoro-λ6-sulfanyl (SF5) Groups [J].
Brel, VK .
SYNTHESIS-STUTTGART, 2005, (08) :1245-1250
[7]   SYNTHESIS AND SPECTROSCOPIC PROPERTIES OF ETHYNYLSULFUR PENTAFLUORIDE (SF5C=CH) [J].
CANICH, JAM ;
LUDVIG, MM ;
PAUDLER, WW ;
GARD, GL ;
SHREEVE, JM .
INORGANIC CHEMISTRY, 1985, 24 (22) :3668-3670
[8]  
CLAIR TL, 1993, Patent No. 5220070
[9]   ORGANOSILICON CHEMISTRY .10. REACTION OF DIAZOMETHYLTRIMETHYLSILANE WITH TRIFLUOROACETONITRILE AND CYANOGEN HALIDES TO GIVE TRIAZOLES [J].
CROSSMAN, JM ;
HASZELDINE, RN ;
TIPPING, AE .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1973, (05) :483-486
[10]   Synthesis of 2-pentafluorosulfanylnaphthalene [J].
Dolbier, William R., Jr. ;
Mitani, Akira ;
Warren, Robin D. .
TETRAHEDRON LETTERS, 2007, 48 (08) :1325-1326
123456