Reaction of imines with N-iodosuccinimide (NIS):: unexpected formation of stable 1:1 complexes

被引:43
作者
Castellote, Isabel
Moron, Maria
Burgos, Carolina [1 ]
Alvarez-Builla, Julio
Martin, Avelino
Gomez-Sal, Pilar
Vaquero, Juan J.
机构
[1] Univ Alcala de Henares, Dept Quim Organ, Madrid 28871, Spain
[2] Univ Alcala de Henares, Dept Quim Inorgan, Madrid 28871, Spain
关键词
D O I
10.1039/b615183c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Imines react with N-iodosuccinimide (NIS) to afford unexpected 1 : 1 complexes and the structure of one of these was determined by single-crystal X-ray diffraction; the reaction seems to be very general for substituted cyclic imines with solid stable complexes obtained in high yields; this is the first reported example of a halogen bonding interaction involving the C = N bond and NIS.
引用
收藏
页码:1281 / 1283
页数:3
相关论文
共 18 条
[1]   Hybrid iodoperfluoroalkane-ferrocene supramolecular arrays: the shortest contacts iodine forms with nitrogen atoms and unsaturated moieties [J].
Amati, M ;
Lelj, F ;
Liantonio, R ;
Metrangolo, P ;
Luzzati, S ;
Pilati, T ;
Resnati, G .
JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (04) :629-640
[2]   Halogen bonds in biological molecules [J].
Auffinger, P ;
Hays, FA ;
Westhof, E ;
Ho, PS .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (48) :16789-16794
[3]   Halogen bonding driven self-assembly of (E)-1,2-diiodo-1,2-difluoroethene with nitrogen substituted hydrocarbons [J].
Burton, DD ;
Fontana, F ;
Metrangolo, P ;
Pilati, T ;
Resnati, G .
TETRAHEDRON LETTERS, 2003, 44 (04) :645-648
[4]   Pyrrolodiazines.: 6.: Palladium-catalyzed arylation, heteroarylation, and amination of 3,4-dihydropyrrolo[1,2-α]pyrazines [J].
Castellote, I ;
Vaquero, JJ ;
Fernández-Gadea, J ;
Alvarez-Builla, J .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8668-8675
[5]  
DeKimpe N, 1997, TETRAHEDRON, V53, P3693
[6]   Perfluorocarbon-hydrocarbon discrete intermolecular aggregates:: An exceptionally short N•••I contact [J].
Fontana, F ;
Forni, A ;
Metrangolo, P ;
Panzeri, W ;
Pilati, T ;
Resnati, G .
SUPRAMOLECULAR CHEMISTRY, 2002, 14 (01) :47-55
[7]  
JIRKOVSKY I, 1981, SYNTHESIS-STUTTGART, P481
[8]  
LIKHOSHERSTOV AM, 1986, ZH ORG KHIM+, V22, P2610
[9]   NEW USES OF THE WESTPHAL CONDENSATION - SYNTHESIS OF PI-DONOR-PI-ACCEPTOR HETEROCYCLES [J].
MATIA, MP ;
EZQUERRA, J ;
SANCHEZFERRANDO, F ;
GARCIANAVIO, JL ;
VAQUERO, JJ ;
ALVAREZBUILLA, J .
TETRAHEDRON, 1991, 47 (35) :7329-7342
[10]  
Metrangolo P, 2001, CHEM-EUR J, V7, P2511, DOI 10.1002/1521-3765(20010618)7:12<2511::AID-CHEM25110>3.0.CO