Synthesis and structure of a novel molecular bowl with an all-carbon and acyclic framework

被引:22
作者
Goto, K [1 ]
Holler, M [1 ]
Okazaki, R [1 ]
机构
[1] UNIV TOKYO,GRAD SCH SCI,DEPT CHEM,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/0040-4039(96)00511-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel all-carbon molecular bowl 2 where the central functionality is surrounded by two rigid tetramethyl-m-terphenyl units was designed. Bromide 3 was readily synthesized by copper (I)-catalyzed coupling reaction between 4 and 5. X-ray crystallographic analysis established that 3 has a bowl-shaped structure although it is an acyclic molecule. Butyl sulfide 6 and thiol 8 were synthesized via lithiation of 3. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:3141 / 3144
页数:4
相关论文
共 11 条
[1]   SYNTHESIS OF A STABLE ARENESULFENIC ACID BEARING A BOWL-SHAPED MACROBICYCLIC CYCLOPHANE SKELETON [J].
GOTO, K ;
TOKITOH, N ;
OKAZAKI, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1124-1126
[2]   SYNTHESIS AND STRUCTURE OF A NOVEL MACROBICYCLIC CYCLOPHANE WITH A MOLECULAR CAVITY [J].
GOTO, K ;
TOKITOH, N ;
GOTO, M ;
OKAZAKI, R .
TETRAHEDRON LETTERS, 1993, 34 (35) :5605-5608
[3]   Concave reagents .16. Concave reagents .17. Steric effects on the acidity of concave sulfinic acids and concave benzoic acids [J].
Luning, U ;
Baumgartner, H ;
Wangnick, C .
TETRAHEDRON, 1996, 52 (02) :599-604
[4]   CONCAVE REAGENTS .7. CONCAVE BENZOIC-ACIDS [J].
LUNING, U ;
WANGNICK, C ;
PETERS, K ;
VONSCHNERING, HG .
CHEMISCHE BERICHTE, 1991, 124 (02) :397-402
[5]  
LUNING U, 1995, TOP CURR CHEM, V175, P57
[6]   MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].
MOHAMADI, F ;
RICHARDS, NGJ ;
GUIDA, WC ;
LISKAMP, R ;
LIPTON, M ;
CAUFIELD, C ;
CHANG, G ;
HENDRICKSON, T ;
STILL, WC .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467
[7]   PROPERTIES OF CHALCOGEN CHALCOGEN BONDS .17. DISULFANE AND TRISULFANE WITH STERICALLY CONGESTED ALKYL SUBSTITUENTS - THE 1ST TRANS-DIALKYLDISULFANE [J].
OSTROWSKI, M ;
JESKE, J ;
JONES, PG ;
DUMONT, WW .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (06) :1355-1359
[8]  
Pope M.T., 1983, HETEROPOLY ISOPOLY O
[9]  
TAMURA M, 1971, SYNTH-INT J METHODS, P303
[10]   METACYCLOPHANES AND RELATED-COMPOUNDS .14. PREPARATION OF 8,16-DIFLUORO[2,2]METACYCLOPHANE [J].
TASHIRO, M ;
YAMATO, T .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2939-2942