REGIOSPECIFIC FUNCTIONALIZATION OF BINOR-S BY A GIF TYPE OXIDATION SYSTEM

被引:14
作者
BARTON, DHR [1 ]
EATON, PE [1 ]
LIU, WG [1 ]
机构
[1] UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
关键词
D O I
10.1016/0040-4039(91)80142-S
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under GoAgg(III) conditions, the saturated heptacyclic hydrocarbon Binor S which contains 12 tertiary and 2 secondary carbons, was regiospecifically oxidized to a single product, the ketone heptacyclo[8.4.0.0(2,7).0(3,5).0(4,8).0(9,13).0(12,14]tetradecane-6-one with good yield. This work represents the first example of a completely regiospecific oxidation of a methylene group into a ketone in the presence of so many saturated tertiary C-H bonds by a Gif type system.
引用
收藏
页码:6263 / 6264
页数:2
相关论文
共 9 条
[1]   THE EFFECT OF LIGAND VARIATION ON THE RATE OF CYCLODODECANE OXIDATION UNDER MODIFIED GO AGG-2 CONDITIONS [J].
ABOUTJAUDET, E ;
BARTON, DHR ;
CSUHAI, E ;
OZBALIK, N .
TETRAHEDRON LETTERS, 1990, 31 (12) :1657-1660
[2]   FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .14. FURTHER-STUDIES ON THE MECHANISM OF GIF-TYPE SYSTEMS [J].
BARTON, DHR ;
HALLEY, F ;
OZBALIK, N ;
SCHMITT, M ;
YOUNG, E ;
BALAVOINE, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7144-7149
[3]   STRUCTURE OF BINOR-S ESTABLISHED FROM DIONE DERIVATIVE - CRYSTAL AND MOLECULAR STRUCTURE OF DECAHYDRO[1,2,4-5,6,8]DIMETHENO-S-INDACENEDIONE [J].
BOER, FP ;
NEUMAN, MA ;
ROTH, RJ ;
KATZ, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (18) :4436-&
[4]   CYTOCHROME-P-450 AND SYNTHETIC MODELS [J].
MANSUY, D .
PURE AND APPLIED CHEMISTRY, 1987, 59 (06) :759-770
[5]  
NAKANO TG, 1987, J AM CHEM SOC, V109, P3625
[6]   REGIOSPECIFIC OXIDATION OF BINOR-S AND ACID-CATALYZED REARRANGEMENT OF THE PRODUCT TO THE 1ST EXAMPLE OF A PENTACYCLO[6.6.0.05,14.07,12.09,13]TETRADECANE [J].
PRAMOD, K ;
EATON, PE ;
GILARDI, R ;
FLIPPENANDERSON, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6105-6107
[7]   COBALT(III) ALKYLPEROXY COMPLEXES - SYNTHESIS, X-RAY STRUCTURE, AND ROLE IN THE CATALYTIC DECOMPOSITION OF ALKYL HYDROPEROXIDES AND IN THE HYDROXYLATION OF HYDROCARBONS [J].
SAUSSINE, L ;
BRAZI, E ;
ROBINE, A ;
MIMOUN, H ;
FISCHER, J ;
WEISS, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3534-3540
[8]   PI-COMPLEX MULTICENTER REACTIONS PROMOTED BY BINUCLEAR CATALYST SYSTEMS . BINOR-S A NEW HEPTACYCLOTETRADECANE VIA STEREOSPECIFIC DIMERIZATION OF BICYCLOHEPTADIENE [J].
SCHRAUZE.GN ;
BASTIAN, BN ;
FOSSELIU.GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (21) :4890-&
[9]  
SCHRAUZE.GN, 1970, TETRAHEDRON LETT, P543