Bromine Addition to Cyanonorbornene Derivatives
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概要
- 論文の詳細を見る
The addition reactions of <I>endo</I>-5-cyanonorbornene, <I>trans-endo,exo</I>-5,6-dicyanonorhornene, <I>cis-endo</I>-5,6-dicyanonorbornene, and <I>cis-exo</I>-5,6-dicyanonorbornene with bromine have been studied. The assignments of the configurations of bromine adducts were determined mainly on the basis of the NMR spectra. As to <I>trans-endo,exo</I>-5,6-dicyanonorbornene, reaction mixtures have been found to contain <I>trans</I> and <I>exo-cis</I> adducts. The reaction conditions involving the proportions of these isomers and a rationale for the formation of the <I>exo-cis</I> adduct are discussed. <I>cis-endo</I>-5,6-Dicyanonorbornene and <I>cis-endo</I>-5,6-dicyanonorbornene gave the <I>exo-cis</I> adduct and the <I>trans</I> adduct respectively. The stereochemistry of bromine atoms may be explained in terms of a steric factor. A kinetic study showed that these addition reactions in solution in acetic acid obey the second-order rate law and that the magnitudes of the rate constants are in the order; <I>cis-exo</I>-5,6-dicyanonorborne><I>trans-endo,exo</I>-5,6-dicyanonorbornene><I>cis-endo</I>-dicyanonorbornene.
- 公益社団法人 日本化学会の論文
著者
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Nomura Masakatsu
Department Of Applied Chemistry Faculty Of Engineering Osaka University
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Matsubara Masaaki
Department Of Orthopaedic Surgery Nissan Tamagawa Hospital
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Kikkawa Shoichi
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Uno Yoichiro
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Yanagida Yuji
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Matsubara Masaaki
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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