Synthesis of (E,E)- and (Z,Z)-1,5-cycloalkadienes by means of the electrochemical cyclization of allylic 1,.OMEGA.-dibromides.

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概要

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• Electrolysis of (<I>E</I>,<I>E</I>)-1,<I>n</I>-dibromo-2,(<I>n</I>-2)-alkadienes (<I>n</I>=12, 14) in tetrahydrofuran gave the corresponding twelve or fourteen-membered (<I>E</I>,<I>E</I>)-1,5-cycloalkadienes, albeit in low yields, together with (<I>E</I>)-4-vinylcycloalkenes and isomeric alkadienes. Similar electrolysis of (<I>Z</I>,<I>Z</I>)-1,<I>n</I>-dibromo-2,(<I>n</I>-2)-alkadienes (<I>n</I>=10, 12, 14) gave the corresponding ten, twelve, or fourteen-membered (<I>Z</I>,<I>Z</I>)-1,5-cycloalkadienes in 11 to 13% yields, with the accompanying formation of (<I>Z</I>)-4-vinylcycloalkenes and isomeric alkadienes.

• 公益社団法人 日本化学会の論文

著者

• Suginome Hiroshi

  Division of Organic Synthesis, Department of Chemical Process Engineering, Faculty of Engineering, Hokkaido University

関連論文

• Synthesis of (E,E)- and (Z,Z)-1,5-cycloalkadienes by means of the electrochemical cyclization of allylic 1,.OMEGA.-dibromides.

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