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Title of article :
Zirconium-catalyzed chemoselective methylalumination of ethers, amines, and sulfides bearing two terminal alkenyl groups
Author/Authors :
Ryukichi Takagi، نويسنده , , Nao Igata، نويسنده , , Kazuhiro Yamamoto، نويسنده , , Satoshi Kojima، نويسنده ,
Issue Information :
دوفصلنامه با شماره پیاپی سال 2011
Pages :
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Abstract :
Chemoselectivity in the methylalumination reaction of unsymmetrical ethers, amines, and sulfides bearing two different terminal alkenyl groups, a 13-tetradecenyl group and an allyl, 4-pentenyl or 6-heptenyl group was examined. The methylalumination of the allyl derivatives proceeded with complete chemoselectivity to afford only the 13-tetradecenyl-monomethylated products. In the methylalumination reactions of the 4-pentenyl and the 6-heptenyl derivatives, in addition to the 13-tetradecenyl-monomethylated products, and dimethylated products were also obtained. However, as in the case of the allyl derivatives, monomethylation to the shorter 4-pentenyl or 6-heptenyl group was not observed, except in the case of 6-heptenyl 13-tetradecenyl amine. The unique selectivity was rationalized upon how readily the intramolecular ligand exchange reaction between intermediate zirconocenium–alkene and zirconocenium–heteroatom complexes could occur.
Keywords :
Heteroatom , Chemoselectivity , Zr-catalyzed methylalumination
Journal title :
Journal of Organometallic Chemistry
Link To Document :