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 language | English |
|---|---|
| Pages (from-to) | 2383-2390 |
| Number of pages | 8 |
| Journal | Journal of the Chemical Society - Perkin Transactions 1 |
| Issue number | 16 |
| DOIs | |
| Publication status | Published - 1999 Jan 1 |
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Cite this
Face selectivity in the reactions of Grignard reagents with 5-substituted-2-dicyanomethyIeneadamantanes. / Kao, Kuo Hsi; Siicu, Ren Shyang; Clicn, Yuh Shih; Lin, Wen Wci; Liu, Ju Tsung; Ching-FaYao.
In: Journal of the Chemical Society - Perkin Transactions 1, No. 16, 01.01.1999, p. 2383-2390.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Face selectivity in the reactions of Grignard reagents with 5-substituted-2-dicyanomethyIeneadamantanes
AU - Kao, Kuo Hsi
AU - Siicu, Ren Shyang
AU - Clicn, Yuh Shih
AU - Lin, Wen Wci
AU - Liu, Ju Tsung
AU - Ching-FaYao,
PY - 1999/1/1
Y1 - 1999/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=33746458853&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33746458853&partnerID=8YFLogxK
U2 - 10.1039/a901484e
DO - 10.1039/a901484e
M3 - Article
AN - SCOPUS:33746458853
SP - 2383
EP - 2390
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1470-4358
IS - 16
ER -