Highly stereoselective isomerization of monosubstituted 1-alkenes to (E)-2-alkenes by catalysis of (C5Me5)2TiCl2/NaC10H8.
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概要
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The catalyst systems which consist of MCl<SUB>2</SUB>(C<SUB>5</SUB>R<SUB>5</SUB>)<SUB>2</SUB>(M=Ti, Zr; R=H, CH<SUB>3</SUB>)/NaC<SUB>10</SUB>H<SUB>8</SUB>, <I>i</I>-C<SUB>3</SUB>H<SUB>7</SUB>MgBr, <I>n</I>-C<SUB>4</SUB>H<SUB>9</SUB>Li or LiAlH<SUB>4</SUB> in 1 : 2 ratio were highly effective for the stereoselective isomerization of monosubstituted 1-alkenes to (<I>E</I>)-2-alkenes. Unconjugated dienes were converted to (<I>E</I>)- or (<I>E</I>,<I>E</I>)-dienes. The catalysis of (C<SUB>5</SUB>Me<SUB>5</SUB>)TiCl<SUB>2</SUB>/NaC<SUB>10</SUB>H<SUB>8</SUB> was extremely high and resulted in the complete isomerization of 1-alkenes in >99% stereoselectivity within a short period. The use of the bulky C<SUB>5</SUB>Me<SUB>5</SUB> ligand is essential to find out the excellent stereoselectivity. Systems, (C<SUB>5</SUB>H<SUB>5</SUB>)<SUB>2</SUB>TiCl<SUB>2</SUB>/NaC<SUB>10</SUB>H<SUB>8</SUB> and (C<SUB>5</SUB>H<SUB>5</SUB>)<SUB>2</SUB>TiCl<SUB>2</SUB>/<I>i</I>-C<SUB>3</SUB>H<SUB>7</SUB>MgBr showed less selectivity and the catalysis of the corresponding zirconium systems was very poor irrespective of the reducing agents and substrates.
- 公益社団法人 日本化学会の論文
著者
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Yasuda Hajime
Department Of Applied Chemistry Faculty Of Engineering Hiroshima University
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Nakamura Akira
Department Oc Macromolecular Science Faculty Of Science Osaka University
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Akita Munetaka
Department of Macromolecular Science, Faculty of Science, Osaka University
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Nagasuna Kinya
Department of Macromolecular Science, Faculty of Science, Osaka University
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