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Phil Ho Lee*,Eunkyong Shim,이구연,Dong Seomoon,Sundae Kim 대한화학회 2005 Bulletin of the Korean Chemical Society Vol.26 No.1
Allylindium and propargylindium reagents in situ generated from the reactions of indium with allyl halides and propargyl halides could participate as nucleophiles in Pd-catalyzed substitution reactions of allyl carbonates to produce 1,5-dienes and 1,5-enynes in good yields. β-Hydride elimination products were produced in case of carbonates having β-hydrogens. Because organoindium reagents obtained from allyl or propargyl halides and indium have previously not been used to Pd-catalyzed allylic and propargylic substitution reactions, these results should provide more opportunities for the development of new C-C bond forming reactions.
Regioselective Addition Reactions of the Organoindium Reagents onto α, β-Unsaturated Ketones
이필호,Hyun Kim,이구연,Dong Seomoon,Sundae Kim,Heechul Kim,Hyunseok Kim,Miae Lee,Eunkyong Shim,Seokju Lee,Misook Kim,Mijeong Han,Kwanghyun Noh,Madabhushi Sridhar 대한화학회 2004 Bulletin of the Korean Chemical Society Vol.25 No.11
Regioselectivity on the reactions of α,β-enones with organoindium such as in situ generated allylindium and allenylindium was systematically studied in the presence of TMSCl as an additive. Treatment of 2-cyclohexen- 1-one, carvone, 2-cyclohepten-1-one, and chalcone with allylindium reagent produced 1,4-addition products in good yields, while 2-cyclopenten-1-one, 2-methyl-2-cyclopenten-1-one, 4,4-dimethylcyclohexen-1-one, 3- nonen-2-one, 4-hexen-3-one, and 4-phenyl-3-buten-2-one afforded 1,2-addition products. Indium reagent derived from indium and propargyl bromide in Grignard type gave addition products in good yields, under which the successive addition of α,β-enone and TMSCl were necessary. Although organoindium reagent derived from propargyl bromide produced propargylated compound in Grignard type except 2-cyclohepten-1- one, indium reagent obtained from 1-bromo-2-butyne having γ-methyl group gave allenylated product in Barbier type.