Restricted rotation involving the tetrahedral carbon.: LXIV.: Barriers to rotation of s-alkyl groups in 9-s-alkyl-8,13-difluoro-1,4-dimethyl- and 1,2,3,4-tetrachloro-triptycenes

被引:6
作者
Oki, M [1 ]
Nishino, M [1 ]
Kaieda, K [1 ]
Nakashima, T [1 ]
Toyota, S [1 ]
机构
[1] Okayama Univ Sci, Fac Sci, Dept Chem, Okayama 7000005, Japan
关键词
D O I
10.1246/bcsj.74.357
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
9-(3-Acetoxy-1-methylpropyl)-8,13-difluoro-1,4-dimethyltriptycene and 9-(1-methyl-2-propenyl)-8,13-difluoro-1,4-dimethyl- and 1,2,3,4-tetrachloro-triptycenes were prepared. Their barriers to internal rotation around the C(9)-C(alkyl) bonds were measured by the classical kinetics. The barrier was affected a little by the substituent, being ca. 25-26 kcal mol(-1). Rotamer distributions in these compounds and possible causes for these indifferent barriers to rotation are discussed.
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收藏
页码:357 / 361
页数:5
相关论文
共 21 条
[1]   INTRAMOLECULAR MOBILITY IN 9-ARYLFLUORENES .1. NATURE OF EXCHANGE PROCESS FOR MAGNETICALLY NONEQUIVALENT PAIRS OF ATOMS [J].
ALBERT, K ;
RIEKER, A .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (05) :1804-1822
[2]   SOME 9-ARYLFLUORENES . RING-CURRENT EFFECTS ON NUCLEAR MAGNETIC RESONANCE SPECTRA CARBONIUM IONS AND 9-MESITYLFLUORENYL RADICAL [J].
CHANDROSS, EA ;
SHELEY, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (16) :4345-+
[3]  
GRONOWIT.S, 1967, ARK KEMI, V27, P145
[4]   RESTRICTED ROTATION INVOLVING THE TETRAHEDRAL CARBON .40. BARRIERS TO ROTATION OF 9-(1-METHYL-2-PROPENYL)TRIPTYCENES [J].
KIKUCHI, H ;
HATAKEYAMA, S ;
YAMAMOTO, G ;
OKI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (12) :3832-3836
[5]   RESTRICTED ROTATION INVOLVING THE TETRAHEDRAL CARBON .38. BARRIERS TO ROTATION AND POPULATION-DISTRIBUTIONS OF 9-(8-METHYL-1-NAPHTHYL)FLUORENE AND ITS 1-METHYL DERIVATIVE [J].
MORI, T ;
OKI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (04) :1199-1202
[6]   RESTRICTED ROTATION INVOLVING THE TETRAHEDRAL CARBON .44. THE EFFECTS OF 1-SUBSTITUENTS ON THE BARRIERS TO ROTATION IN 9-(2-METHYL-1-NAPHTHYL)FLUORENES [J].
MURATA, S ;
MORI, T ;
OKI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (07) :1970-1975
[7]   IMPLICATIONS OF UNUSUAL POPULATION RATIOS IN ROTATIONAL ISOMERS OF 9-(4-SUBSTITUTED BENZYL)-8,13-DICHLORO-1,4-DIMETHYLTRIPTYCENES AND 4-SUBSTITUTED 9-BENZYL-8,13-DICHLORO-1-METHYLTRIPTYCENES - CH3...PI HYDROGEN-BOND [J].
NAKAI, Y ;
INOUE, K ;
YAMAMOTO, G ;
OKI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (09) :2923-2931
[8]  
NISHIO M, 1998, CH MU INTERACTIONS E
[9]   RESTRICTED ROTATION INVOLVING THE TETRAHEDRAL CARBON .62. ROTATIONAL-ISOMERISM, STRUCTURE, AND ISOLATION OF TRIPTYCENE ROTAMERS THAT CARRY SECONDARY ALKYL GROUP AT 9-POSITION [J].
OKI, M ;
MATSUSUE, M ;
AKINAGA, T ;
MATSUMOTO, Y ;
TOYOTA, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (10) :2831-2837
[10]   Restricted rotation involving the tetrahedral carbon .63. Endeavor toward enhancing the rotational barrier in 9-s-alkyltriptycenes [J].
Oki, M ;
Fukuda, T ;
Asakura, M ;
Toyota, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (11) :3267-3272