First synthesis of exomethylene paracyclophanes and their structural properties

被引:36
作者
Saito, S [1 ]
Tsuboya, N [1 ]
Yamamoto, Y [1 ]
机构
[1] TOHOKU UNIV,GRAD SCH SCI,DEPT CHEM,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1021/jo970727e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel exomethylene paracyclophanes was synthesized by the intramolecular benzannulation of conjugated enynes in the presence of tetrakis(triphenylphosphine)palladium(0) Detailed spectral studies revealed that the conformation of the exomethylene paracyclophanes depends on the size of the ring; the alkene moiety does not conjugate with the adjacent phenyl group in the smaller exomethylene paracyclophanes.
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收藏
页码:5042 / 5047
页数:6
相关论文
共 21 条
[1]   CONFORMATIONAL-ANALYSIS .87. SYNTHESIS OF A [7]PARACYCLOPHANE [J].
ALLINGER, NL ;
WALTER, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (26) :9267-9268
[2]   MOLECULAR STRUCTURE AND ELECTRONIC SPECTRUM OF[8]PARACYCLOPHANE - A NEW SYNTHETIC METHOD FORPREPARATION OF STRAINED LARGE RINGS [J].
ALLINGER, NL ;
MILLER, MA ;
FREIBERG, LA ;
HERMANN, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (08) :1171-&
[3]   SYNTHESIS OF PARA-BRIDGED BENZENE COMPOUNDS .3. [J].
BARTLETT, MF ;
FIGDOR, SK ;
WIESNER, K .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1952, 30 (04) :291-294
[4]   CROSS-BREEDING REACTION, A BENT BENZENE RING, AND A MULTIPLE DIELS-ALDER REACTION [J].
CRAM, DJ ;
KNOX, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (09) :2204-&
[5]   MACRO RINGS .5. TRANSANNULAR EFFECTS IN THE 1,4-DECAMETHYLENEBENZENE SERIES [J].
CRAM, DJ ;
DAENIKER, HU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (10) :2743-2752
[6]  
FOGTLE JP, 1993, CYCLOPHANE CHEM
[7]  
GEVORGYAN V, UNPUB
[8]   PHOTOCHEMISTRY OF LARGE-RING 2-PHENYLCYCLOALKANONES IN VARIOUS ENVIRONMENTS - INTRAMOLECULAR PARA COUPLING PRODUCTS OF ACYL BENZYL BIRADICALS [J].
HAN, NH ;
LEI, XG ;
TURRO, NJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2927-2930
[9]  
Heck R.F., 1985, PALLADIUM REAGENTS O
[10]  
HUISGEN VR, 1952, LIEBIGS ANN CHEM, V586, P52