Solid-phase oxidative halodecarboxylation of β-arylacrylic acids with the ceric ammonium nitrate-alkali halide system

被引:13
作者
Nikishin, G. I. [1 ]
Sokova, L. L. [1 ]
Makhaev, V. D. [2 ]
Kapustina, N. I. [1 ]
机构
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Moscow Region, Russia
基金
俄罗斯基础研究基金会;
关键词
cinnamic acids; benzaldehydes; ceric ammonium nitrate; beta-halostyrenes; halodecarboxylation; nitrodecarboxylation; solid-phase reactions; mechanochemical activation;
D O I
10.1007/s11172-008-0018-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The solid-phase oxidation of cinnamic, 4-methoxy- and 3,4-dimethoxycinnamic acids with Ce(NH4)(2)(NO3)(6)-MHal system leads to beta-halostyrenes. Similar procedure in the absence of a metal halide results in a cleavage of the C=C bond giving the corresponding benzaldehydes.
引用
收藏
页码:118 / 123
页数:6
相关论文
共 22 条
[1]   SELECTIVITY AND MECHANISM IN THE SIDE-CHAIN HALOGENATION OF METHYLBENZENES PROMOTED PHOTOCHEMICALLY AND BY METAL-COMPLEXES IN THE PRESENCE OF HALIDE-IONS [J].
BACIOCCHI, E ;
CRESCENZI, M .
TETRAHEDRON, 1988, 44 (20) :6525-6536
[2]  
BEHERA GB, 1975, J INDIAN CHEM SOC L, V11, P1056
[3]   Solvent-free oxidation of aliphatic alcohols with ceric ammonium nitrate - lithium bromide system [J].
Kapustina, N. I. ;
Sokova, L. L. ;
Gasanov, R. G. ;
Nikishin, G. I. .
RUSSIAN CHEMICAL BULLETIN, 2007, 56 (08) :1501-1506
[4]   Oxidation of aliphatic alcohols with the lead tetraacetate - metal halide system under mechanical activation [J].
Kapustina, NI ;
Sokova, LL ;
Makhaev, VD ;
Borisov, AP ;
Nikishin, GI .
RUSSIAN CHEMICAL BULLETIN, 2000, 49 (11) :1842-1845
[5]   Recent advances in synthetic transformations mediated by cerium(IV) ammonium nitrate [J].
Nair, V ;
Balagopal, L ;
Rajan, R ;
Mathew, J .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (01) :21-30
[6]   Carbon-heteroatom bond-forming reactions mediated by cerium(IV) ammonium nitrate: An overview [J].
Nair, V ;
Panicker, SB ;
Nair, LG ;
George, TG ;
Augustine, A .
SYNLETT, 2003, (02) :156-165
[7]   An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide [J].
Nair, V ;
Panicker, SB ;
Augustine, A ;
George, TG ;
Thomas, S ;
Vairamani, M .
TETRAHEDRON, 2001, 57 (34) :7417-7422
[8]   Solid-state chlorodecarboxylation of mono- and dicarboxylic acids with the Pb(OAc)4-MCI system [J].
Nikishin, GI ;
Sokova, LL ;
Chizhov, AO ;
Makhaev, VD ;
Kapustina, NI .
RUSSIAN CHEMICAL BULLETIN, 2004, 53 (10) :2200-2204
[9]   Solid-phase oxoalkylation of pyridines and quinolines with 1-methylcycloalkanols under the action of lead tetraacetate [J].
Nikishin, GI ;
Sokova, LL ;
Kapustina, NI .
RUSSIAN CHEMICAL BULLETIN, 2002, 51 (10) :1812-1816
[10]   Addition reactions of unsaturated alpha-ketonic acids. IV [J].
Reimer, M ;
Tobin, E ;
Schaffner, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1935, 57 (01) :211-215