Catalytic amination of unsaturated hydrocarbons:: reactions of p-nitrophenylazide with alkenes catalysed by metallo-porphyrins

被引:70
作者
Cenini, S [1 ]
Tollari, S [1 ]
Penoni, A [1 ]
Cereda, C [1 ]
机构
[1] Ctr CNR, I-20133 Milan, Italy
关键词
alkenes; amination; organic azides; metallo-porphyrins;
D O I
10.1016/S1381-1169(98)00116-2
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Porphyrin derivatives of transition metals such as Ru(TPP)CO, Ru(OEP)CO and Co(OEP)(TPP = dianion of 5, 10, 15, 20-tetraphenylporphyrin, OEP=dianion of 2, 3, 7, 8, 12, 13, 17, 18-octaetylporphyrin) catalyse the reaction of p-nitrophenylazide with cyclohexene to give the corresponding allylamine in good yields. With other olefins such as cyclooctene, 1-octene, styrene and substituted styrenes the main product becomes the corresponding aziridine. The reaction of p-nitrophenylazide with Ru(TPP)CO has been investigated and the mechanism of the catalytic reactions is discussed. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:135 / 146
页数:12
相关论文
共 23 条
[1]   A SIMPLIFIED SYNTHESIS FOR MESO-TETRAPHENYLPORPHIN [J].
ADLER, AD ;
LONGO, FR ;
FINARELLI, JD ;
GOLDMACH.J ;
ASSOUR, J ;
KORSAKOF.L .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) :476-+
[2]  
[Anonymous], 1994, METALLOPORPHYRINS CA
[3]  
AU SM, 1997, CHEM COMMUN, P1665
[4]   Tetraalkylammonium N-chloro-p-toluenesulfonamide as aminating agent of olefins [J].
Cenini, S ;
Penoni, A ;
Tollari, S .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 124 (2-3) :109-113
[5]   Allylic: Amination of cyclohexene catalyzed by ruthenium complexes. A new reaction involving an intermolecular C-H functionalization [J].
Cenini, S ;
Ragaini, F ;
Tollari, S ;
Paone, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) :11964-11965
[6]   OXYGENATION OF HYDROCARBONS BY CYTOCHROME-P-450 MODEL COMPOUNDS - MODIFICATION OF REACTIVITY BY AXIAL LIGANDS [J].
COLLMAN, JP ;
KODADEK, T ;
RAYBUCK, SA ;
MEUNIER, B .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-PHYSICAL SCIENCES, 1983, 80 (22) :7039-7041
[7]  
EVANS DA, 1994, J AM CHEM SOC, V116, P2742
[8]   MECHANISTIC ASPECTS OF IRON-CATALYZED ALLYLIC AMINATION [J].
JOHANNSEN, M ;
JORGENSEN, KA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5979-5982
[9]   A SIMPLE ALLYLIC AMINATION PROCEDURE AND THE METATHESIS OF N-SULFINYLCARBAMATES [J].
KATZ, TJ ;
SHI, SH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (26) :8297-8298
[10]   Arylimido complexes of ruthenium(IV) porphyrins [J].
Leung, WH ;
Hun, TSM ;
Hou, HW ;
Wong, KY .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (02) :237-243