REACTIVITIES OF STABLE ROTAMERS .30. BROMINE ADDITION TO ROTAMERIC 1-(9-FLUORENYL)-2-(1-METHYLVINYL)NAPHTHALENE - FATE OF INTERMEDIATE CATIONS PRODUCED BY BROMINE CATION ATTACK

被引:2
作者
OKI, M
SHIONOIRI, K
OTAKE, K
ONO, M
TOYOTA, S
机构
关键词
D O I
10.1246/cl.1991.597
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of the rotamers of the title compound with bromine afforded a normal addition compound in the case of ap, whereas the sp rotamer did bromo-olefins and a cyclic compound only. The results are discussed on the basis of the steric effects and pi-participation of the fluorene ring in the case of sp that is not possible in the case of ap. Cation was produced from the bromine adduct of the sp form and the fate of the cation is discussed by comparing with that of the ap.
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页码:597 / 600
页数:4
相关论文
共 10 条
[1]   NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY - STEREOSPECIFICITY OF LONG-RANGE SPIN-SPIN COUPLING IN 1,2-DIBROMO-2-PHENYLPROPANE [J].
DAVIS, DR ;
ROBERTS, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (11) :2252-&
[2]  
MORIYAMA K, 1987, GAZZ CHIM ITAL, V117, P655
[3]   REACTIVITIES OF STABLE ROTAMERS .9. IONIZING REACTIONS OF 9-(2-BROMOMETHYL-6-METHYLPHENYL)FLUORENE ROTAMERS [J].
MURATA, S ;
KANNO, S ;
TANABE, Y ;
NAKAMURA, M ;
OKI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (05) :1522-1530
[4]   REACTIVITIES OF STABLE ROTAMERS .29. METHYL-GROUP CAN STABILIZE CARBOCATIONS [J].
OKI, M ;
TAGUCHI, Y ;
TOYOTA, S ;
YONEMOTO, K ;
YAMAMOTO, G .
CHEMISTRY LETTERS, 1990, (12) :2209-2212
[5]   REACTIVITIES OF STABLE ROTAMERS .23. SOME ADDITION-REACTIONS TOWARD THE VINYL GROUP IN 9-(2-VINYL-1-NAPHTHYL)-FLUORENE ROTAMERS [J].
OKI, M ;
TSUKAHARA, J ;
SONODA, Y ;
MORIYAMA, K ;
NAKAMURA, N .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (12) :4303-4308
[6]   REACTIVITIES OF STABLE ROTAMERS .18. REACTIONS OF 9-[2-(1-HYDROXYETHYL)-1-NAPHTHYL]FLUORENE ROTAMERS WITH SULFURIC-ACID AND THIONYL CHLORIDE [J].
OKI, M ;
TSUKAHARA, J ;
MORIYAMA, K ;
NAKAMURA, N .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (01) :223-228
[8]   STABLE CARBOCATIONS .125. PROTON AND C-13 MAGNETIC-RESONANCE STUDIES OF PHENYLCARBONIUM IONS (BENZYL CATIONS) - EFFECT OF SUBSTITUENTS ON STABILITY OF CARBOCATIONS [J].
OLAH, GA ;
PORTER, RD ;
WHITE, AM ;
JEUELL, CL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) :2044-&
[9]   POLAR ADDITIONS TO STYRENE AND 2-BUTENE SYSTEMS .2. MEDIUM DEPENDENCE OF BROMINATION PRODUCTS [J].
ROLSTON, JH ;
YATES, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (06) :1477-&
[10]   REACTIVITIES OF STABLE ROTAMERS .11. ROTAMER DISTRIBUTIONS AND SOME ADDITION-REACTIONS TO THE CARBONYL IN 9-[2-(SUBSTITUTED CARBONYL)-1-NAPHTHYL]FLUORENE ROTAMERS [J].
SAITO, R ;
OKI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (10) :3273-3276