TRANSITION-METAL CATALYZED OXIDATIONS .3. REACTION OF 4-HYDROXY[2.2]PARACYCLOPHANE WITH THE MIMOUN MOLYBDENUM OXODIPEROXO COMPLEX [MO(O2)2O].PY.HMPT

被引:36
作者
KROHN, K [1 ]
RIEGER, H [1 ]
HOPF, H [1 ]
BARRETT, D [1 ]
JONES, PG [1 ]
DORING, D [1 ]
机构
[1] TECH UNIV CAROLO WILHELMINA BRAUNSCHWEIG,INST ANORGAN & ANALYT CHEM,W-3300 BRAUNSCHWEIG,GERMANY
关键词
Bicyclo[2.2.1]heptanes; Cage compounds; Norbornanes; Ozonization; Tricyclo[5.2.1.0[!sup]2,6[!/sup]]decanes;
D O I
10.1002/cber.19901230824
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A four‐step preparation of dimethyl 7‐oxobicyclo[2.2.1]‐heptane‐exo‐2, exo‐3‐dicarboxylate (4) in satisfactory yield from the readily available 6,6‐dimethylfulvene and maleic anhydride is described. Compound 4 represents a well‐functionalized intermediate for the synthesis of norbornane derivatives which is used for an improved synthesis of the tricyclic diester 7, precursor of the cage compound 8. An alternative approach to diester 7 from dimethyl 7‐isopropylidenebicyclo[2.2.1]heptane‐exo‐2, exo‐3‐dicarboxylate (2) is also discussed. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
引用
收藏
页码:1729 / 1732
页数:4
相关论文
共 22 条
[1]   OXIDATION OF PHENOLS TO ORTHO-QUINONES USING DIPHENYLSELENINIC ANHYDRIDE [J].
BARTON, DHR ;
BREWSTER, AG ;
LEY, SV ;
ROSENFELD, MN .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (23) :985-986
[2]  
BROSER E, 1984, TETRAHEDRON LETT, V23, P2463
[3]   STUDIES ON THE MECHANISM OF THE ASYMMETRIC EPOXIDATION - A LIGAND VARIATION APPROACH [J].
CARLIER, PR ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4016-4018
[4]   MACRO RINGS .31. QUINONE DERIVED FROM [2.2]PARACYCLOPHANE AN INTRAMOLECULAR-MOLECULAR COMPLEX [J].
CRAM, DJ ;
DAY, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (04) :1227-&
[5]   MACRO RINGS .12. STEREOCHEMICAL CONSEQUENCES OF STERIC COMPRESSION IN THE SMALLEST PARACYCLOPHANE [J].
CRAM, DJ ;
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) :6289-6294
[6]   ENOLETHER .19. INVESTIGATIONS OF THE AUTOXIDATION AND THE REARRANGEMENT OF [N](2,4)PHLOROGLUCINOPHANES [J].
EFFENBERGER, F ;
SPACHMANN, B ;
SCHONWALDER, KH .
CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (10) :1947-1953
[7]  
Finn M. G., 1985, ASYMMETRIC SYNTHESIS, V5, P247
[8]   ASYMMETRIC-SYNTHESIS OF ALPHA-HYDROXY-ESTERS VIA ESTER ENOLATES WITH VERY HIGH DIASTEREOSELECTIVITY [J].
GAMBONI, R ;
TAMM, C .
HELVETICA CHIMICA ACTA, 1986, 69 (03) :615-620
[9]   SIMPLE PROCEDURE FOR THE CONVERSION OF ARYL HALIDES TO THE CORRESPONDING PHENOLS [J].
HAWTHORNE, MF .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (08) :1001-1001
[10]  
HOPF H, 1983, CYCLOPHANES, V1, P521