Synthesis and structure of bishomohexaprismanedione

被引:19
作者
Golobish, TD [1 ]
Dailey, WP [1 ]
机构
[1] UNIV PENN,DEPT CHEM,PHILADELPHIA,PA 19104
关键词
D O I
10.1016/0040-4039(96)00532-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of bishomohexaprimanedione, the D-2h dimer of norbornadienone and a potential precursor to hexaprismane, is reported. The synthesis includes an unusual ring contraction of a cycloalkene using a cis-hydroxylation/periodate cleavage/aldol sequence. The structure of bishomohexaprimanedione determined from single crystal x-ray analysis is well reproduced by ab initio calculations. (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:3239 / 3242
页数:4
相关论文
共 15 条
[1]   THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
TETRAHEDRON, 1985, 41 (19) :3901-3924
[2]   THE SYNTHESIS OF PENTAPRISMANE [J].
EATON, PE ;
OR, YS ;
BRANCA, SJ ;
SHANKAR, BKR .
TETRAHEDRON, 1986, 42 (06) :1621-1631
[3]   CUBANE [J].
EATON, PE ;
COLE, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (15) :3157-&
[4]   PENTAPRISMANE [J].
EATON, PE ;
OR, YS ;
BRANCA, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2134-2136
[5]   CONVENIENT SYNTHESIS OF THE 1,4-BISHOMO-6-SECOHEPTAPRISMANE RING-SYSTEM [J].
FORMAN, MA ;
DAILEY, WP .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1501-1507
[6]   THE SYNTHESIS AND REACTIONS OF PRISMANES RECENT DEVELOPMENTS [J].
FORMAN, MA ;
DAILEY, WP .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (03) :291-320
[7]   SYNTHESIS OF PRISMANE [J].
KATZ, TJ ;
ACTON, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) :2738-2739
[8]   SYNTHETIC STUDIES TOWARDS PRISMANES - SECO-(6)-PRISMANE [J].
MEHTA, G ;
PADMA, S .
TETRAHEDRON, 1991, 47 (37) :7783-7806
[9]   SYNTHETIC STUDIES TOWARDS PRISMANES - 1,4-BISHOMO-[6]-PRISMANE (GARUDANE) [J].
MEHTA, G ;
PADMA, S .
TETRAHEDRON, 1991, 47 (37) :7807-7820
[10]   D2H-BISHOMOHEXAPRISMANE (GARUDANE) - DESIGN OF THE FACE-TO-FACE 2+2 DIMER OF NORBORNADIENE [J].
MEHTA, G ;
PADMA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7230-7232