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À propos de : Reaction of 1,4-Dibromo-2,3-dihydroxynaphthalene with2-Naphthoxide Ion. Solvent and Cation Control in the Formationof the Conformationally Locked Stereoisomers of2,2‘,3‘,2‘‘-Tetrahydroxy-1,1‘:4‘,1‘‘-ternaphthyl and2,2‘,3‘,2‘‘,3‘‘,2‘‘‘-Hexahydroxy-1,1‘:4‘,1‘‘:4‘‘,1‘‘‘-quaternaphthyl        

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  • Reaction of 1,4-Dibromo-2,3-dihydroxynaphthalene with2-Naphthoxide Ion. Solvent and Cation Control in the Formationof the Conformationally Locked Stereoisomers of2,2‘,3‘,2‘‘-Tetrahydroxy-1,1‘:4‘,1‘‘-ternaphthyl and2,2‘,3‘,2‘‘,3‘‘,2‘‘‘-Hexahydroxy-1,1‘:4‘,1‘‘:4‘‘,1‘‘‘-quaternaphthyl
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  • The reaction of the dibromide 1 with the 2-naphthoxideion 2 proceeds under remarkably mildconditions (25−50 °C), yielding all possible stereoisomers ofternaphthol 3 and quaternaphthol 4.An unambiguous structure assignment has been made for theindividual stereoisomers andconditions for their thermal interconversion have been established.In contrast to a nonselectivedistribution of stereoisomers found in the thermodynamic equilibriummixture, a high stereoselectivity can be induced in the coupling reaction under kineticcontrol. The coordinating abilityof the alkali metal counterion (M+) of the participating2-naphthoxide ion 2 has been found to playa key role in the stereocontrol, supporting strongly the formation ofthe cis stereoisomers of 3 and4. When the coordinating ability of M+ issuppressed by an efficient solvation and/or bycomplexationwith 18-crown-6, formation of the trans stereoisomersprevails in the reaction.
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