Mechanisms of imine exchange reactions in organic solvents

被引:262
作者
Ciaccia, Maria
Di Stefano, Stefano [1 ]
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
关键词
NUCLEOPHILIC CATALYSIS; METATHESIS REACTIONS; ADDITIVE FORMATION; 4-MEMBERED RINGS; DRIVEN EVOLUTION; PROTON-TRANSFER; TRANSIMINATION; SOLVATION; MILD; DERIVATIVES;
D O I
10.1039/c4ob02110j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The state of the art in the mechanisms operating in imine chemistry in organic solvents is critically discussed in the present review. In particular, the reaction pathways involved in imine formation, transimination and imine metathesis in organic media are taken into account, with the aim of organizing the poor, and sometimes scattered, information available in the literature. It is shown that 4-membered cyclic transition states, either polar or apolar, can be considered a leitmotif for the chemistry of imines in organic solvents. However, it is pointed out that further investigations will be necessary to reach an adequate degree of knowledge of the mechanisms involved in such important reversible processes.
引用
收藏
页码:646 / 654
页数:9
相关论文
共 86 条
[1]  
Anslyn E. V., 2006, MODERN PHYS ORGANIC, P597
[2]   Dynamic imine chemistry [J].
Belowich, Matthew E. ;
Stoddart, J. Fraser .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (06) :2003-2024
[3]   Mechanisms of Autocatalysis [J].
Bissette, Andrew J. ;
Fletcher, Stephen P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) :12800-12826
[4]   Use of niobium(III) and niobium(V) compounds in catalytic imine metathesis under mild conditions [J].
Bruno, JW ;
Li, XJ .
ORGANOMETALLICS, 2000, 19 (23) :4672-4674
[5]   Role of trace amine in the metathesis of imines by CpTa(=NR)Cl2 [J].
Burland, MC ;
Pontz, TW ;
Meyer, TY .
ORGANOMETALLICS, 2002, 21 (09) :1933-1941
[6]   Transition-metal-catalyzed imine metathesis [J].
Cantrell, GK ;
Meyer, TY .
ORGANOMETALLICS, 1997, 16 (25) :5381-5383
[7]   Catalytic C=N bond formation by metal-imide-mediated imine metathesis [J].
Cantrell, GK ;
Meyer, TY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8035-8042
[8]   Azaheteroalkene metathesis: Reaction of imines with molybdenum(vi) bis(imide) complexes [J].
Cantrell, GK ;
Meyer, TY .
CHEMICAL COMMUNICATIONS, 1997, (16) :1551-1552
[9]  
Carey R.J., 2007, Advanced Organic Chemistry Part A: Structure and Mechanisms
[10]   C-13 NUCLEAR MAGNETIC-RESONANCE STUDIES OF THE PRODUCTS OF REACTION OF ACETALDEHYDE AND OF SIMPLE KETONES IN LIQUID-AMMONIA, IN HYDRAZINE HYDRATE, AND IN SOME SUBSTITUTED HYDRAZINE SOLUTIONS [J].
CHUDEK, JA ;
FOSTER, R ;
YOUNG, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (08) :1285-1289