Rotational isomerisum in fluorene derivatives XXIII syntheses of 1-substituted 1'-methyl-9, 9'-bifluorenyl derivatives and their conformational isomerisum
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概要
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The reaction of 1-substituted fluorenones (1-substituents: CH_3, F, Cl, Br, I, OCH_3, and Ph) with 1-methyl-9-fluorenyllithium gave a mixture of A (erythro) and B (threo)-isomers of 1-substituted 9-hydroxy-1'-methyl-9, 9'-bifluorenyls (2). In these cases, 2-B-isomers were obtained more abundantly than 2-A-isomers owing to the steric effects between 1-substituents and 1'-CH_3 group. 1-Substituted 1'-methyl-9, 9'-bifluorenyls (3) were prepared from the reduction of 2 with HI (method i) or the reaction of 9-bromo-1-methylfluorene with 1-substituted 9-fluorenyllithium (method ii). In these cases, 3-B-isomers were mainly obtained by method ii, whereas, 3-A-isomers by method i. Furthermore, the restricted rotation about the C(9)-C(9') bonds in 3 were investigated by DNMR method, and we could observe some rocking motion from one gauche form (a) to the other (e) in A-isomers of 1.1'-dimethyl-9, 9'-bifluorenyl (3a) and 1-fluoro-1'-methyl-9, 9'-bifluorenyl (3b).
- 山口大学の論文
著者
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Nishida A
Yamaguchi Univ.
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NISHIDA Akiko
Department of Applied Chemistry and Chemical Engineering
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NISHIYAMA Shinichi
(Present address)Ashimori Kogyo Co., Osaka
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FUJISAKI Shizuo
Department of Applied Chemistry and Chemical Engineering
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Nishiyama Shinichi
(present Address)ashimori Kogyo Co. Osaka
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Fujisaki S
Department Of Applied Chemistry And Chemical Engineering
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Fujisaki Shizuo
Department Industrial Chemistry
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Nishida Akiko
Department Of Anesthesiology Gunma University School Of Medicine
関連論文
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