Macrobicyclic triphosphazides and tri-λ5-phosphazenes derived from PhC(CH2PPh2)3.: Two propeller-shaped diastereoisomers in the crystals

被引:9
作者
Alajarin, Mateo
Lopez-Leonardo, Carmen
Berna, Jose
Steed, Jonathan W.
机构
[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain
[2] Univ Durham, Dept Chem, Durham DH1 3LE, England
关键词
triphosphazide; tri-lambda(5)-phosphazene; macrobicycle; cage-compound; propeller; tripod-tripod coupling;
D O I
10.1016/j.tet.2006.12.027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New macrobicyclic cage-compounds composed of two tripodal, propeller-shaped fragments linked by phosphazide and phosphazene units have been synthesized by reaction of PhC(CH2PPh2)(3) with tris(m-azidobenzyl)amines. Two diastereoisomers of one of these cages have been characterized in the solid state by X-ray crystallography, one presenting two propellers with the same sense of twist P*,P* whereas in the second one the helical sense of both propellers is the opposite, P*,M*. In contrast, only one species is apparent in CDCl3 solution. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2078 / 2083
页数:6
相关论文
共 24 条
[1]   Self-assembly of tris(2-ureidobenzyl)amines:: A new type of capped, capsule-like dimeric aggregates derived from a highly flexible skeleton [J].
Alajarín, M ;
Pastor, A ;
Orenes, RA ;
Steed, JW ;
Arakawa, R .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (06) :1383-1397
[2]   Ab initio SCF-MO study of the Staudinger phosphorylation reaction between a phosphane and an azide to form a phosphazene [J].
Alajarin, M ;
Conesa, C ;
Rzepa, HS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (09) :1811-1814
[3]   Design and synthesis of a new macrobicyclic tris(phosphazide) [J].
Alajarín, M ;
Vidal, A ;
López-Leonardo, C ;
Berná, J ;
de Arellano, MCR .
TETRAHEDRON LETTERS, 1998, 39 (42) :7807-7810
[4]  
Alajarín M, 2002, ANGEW CHEM INT EDIT, V41, P1205, DOI 10.1002/1521-3773(20020402)41:7<1205::AID-ANIE1205>3.0.CO
[5]  
2-X
[6]  
Alajarín M, 1998, CHEM-EUR J, V4, P2558
[7]   New cage compounds: Preparation and characterization of chiral C-3-symmetric macrobicyclic tris(phosphazides) [J].
Alajarin, M ;
Molina, P ;
LopezLazaro, A ;
FocesFoces, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :67-70
[8]   New macrobicyclic triphosphazides and triphosphazenes formed by self-assembly of tripodal triazides with triphosphanes [J].
Alajarin, Mateo ;
Lopez-Leonardo, Carmen ;
Berna, Jose .
TETRAHEDRON, 2006, 62 (26) :6190-6202
[9]   Simultaneous freezing of chirality and in-out conformation of a macropentacyclic cryptand by protonation [J].
Bonnot, C ;
Chambron, JC ;
Espinosa, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) :11412-11413
[10]   RECENT ADVANCES IN THE STAUDINGER REACTION [J].
GOLOLOBOV, YG ;
KASUKHIN, LF .
TETRAHEDRON, 1992, 48 (08) :1353-1406