Face selectivity in the reactions of Grignard reagents with 5-substituted-2-dicyanomethyIeneadamantanes

Kuo Hsi Kao*, Ren Shyang Siicu, Yuh Shih Clicn, Wen Wci Lin, Ju Tsung Liu, Ching-FaYao

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

5 引文 斯高帕斯(Scopus)

摘要

Reactions of 5-substituted-2-dicyanomethyleneadamantanes (4-Z) with benzylmagnesium bromide (C6H5CH2MgBr) or alkylmagnësium halides (RMgX) generated the 1,4-addition (5-Z (R)) and/or the hydrogénation (5-Z (H)) products. A variety of substituents X were used: hydro, fluoro, chloro, bromo and phenyl groups. The generation of the different isomeric products from the :u-face or c/;-face by the transfer of the benzyl or alkyl groups, or the hydride from the Grignard reagents is discussed in terms of the electrostatic field influence and the steric hindrance between the Grignard reagents and the substrate 4-Z. Reactions of 4-Br or 4-Ph with phenylmagnesium bromide generated 1,2-addition products 6-Br, 7-Br or 8-Ph when the intermediate A was added to dry methanol or to dilute ice-cold hydrochloric acid solution.

原文英語
頁(從 - 到)2383-2390
頁數8
期刊Journal of the Chemical Society - Perkin Transactions 1
發行號16
DOIs
出版狀態已發佈 - 1999 一月 1

ASJC Scopus subject areas

  • 化學 (全部)

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