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

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Abstract

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.

Original languageEnglish
Pages (from-to)2383-2390
Number of pages8
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number16
DOIs
Publication statusPublished - 1999 Jan 1

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ASJC Scopus subject areas

  • Chemistry(all)

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