The structure of bicyclic ferrocenylmethylene substituted 2-pyrazolines and their reactions with azodicarboxylic acid N-phenylimide

被引:57
作者
Klimova, EI
García, MM
Berestneva, TK
Toledano, CA
Toskano, RA
Ramírez, LR
机构
[1] Univ Nacl Autonoma Mexico, Fac Quim, Mexico City 04510, DF, Mexico
[2] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
关键词
4+2]-cycloaddition; diastereomeric selectivity; ferrocene; induction; molecular structure; monoene addition; pyrazoline; S-cis-Hetero-1,3-dienes; X-ray structural analysis;
D O I
10.1016/S0022-328X(99)00202-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetrical induction in the synthesis of bicyclic pyrazolines with a ferrocenyl substituent has been studied. A relatively high diastereomeric selectivity in the 'chiral-center-by-a-chiral-center' induction of the 1,2-type has been observed. Molecular geometry of a cis-diastereomer of 1-acetyl-9-ferrocenyl-4-ferrocenylmethylene-1,2-diazabicyclo[4.3.0]non-2-ene has been established. Bicyclic 2-pyrazolines having conjugated ferrocenylmethylene fragments interact with azodicarboxylic acid N-phenylimide to form diene and monoene adducts. (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:106 / 114
页数:9
相关论文
共 16 条
[1]   STEREOSELECTIVE SYNTHESES .8. ABSOLUTE CONFIGURATION OF A 1,2-DISUBSTITUTED FERROCENE DERIVATIVE WITH PLANAR AND CENTRAL ELEMENTS OF CHIRALITY AND MECHANISM OF STEREOSELECTIVE METALATIONS OF OPTICALLY-ACTIVE ALPHA-FERROCENYL TERTIARY-AMINES [J].
BATTELLE, LF ;
BAU, R ;
GOKEL, GW ;
OYAKAWA, RT ;
UGI, IK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :482-486
[2]  
CHEKHLOV AN, 1986, IAN SSSR KH, V3, P701
[4]  
KLIMOVA EI, 1996, IZV AKAD NAUK K, V11, P2743
[5]  
KLIMOVA EI, 1994, KHIM FARM ZH, V28, P33
[6]  
KLIMOVA YI, 1992, KHIM FARM ZH+, V26, P69
[7]  
KLIMOVA YI, 1992, KHIM FARM ZH+, V26, P34
[8]  
NESMEYANOV AN, 1979, IAN SSSR KH, P902
[9]  
NESMEYANOV AN, 1981, IAN SSSR KH, P222
[10]   THE BEHAVIOR OF 2-METHYLENE-3-FERROCENYLMETHYLENECAMPHANE UNDER CONDITIONS LEADING TO THE CYCLODIMERIZATION OF FERROCENYL-1,3-BUTADIENES [J].
POSTNOV, VN ;
KLIMOVA, EI ;
GARCIA, MM ;
MELESHONKOVA, NN ;
RYBAKOV, VV ;
ASLANOV, LA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 476 (02) :189-195