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The Twofold Heck Reaction on 1,2-Dihalocycloalkenes and Subsequent 6π-Electrocyclization of the Resulting (E,Z,E)-1,3,5-Hexatrienes: A New Formal {2+2+2}-Assembly of Six-Membered Rings

Voigt, Katharina ; Zezschwitz, Paultheo von ; Rosauer, Keith ; Lansky, Annegret ; Adams, Amy ; Reiser, Oliver ; Meijere, Armin de



Abstract

1,6-Disubstituted (E,Z,E)-1,3,5-hexatrienes (4 and 5) were prepared by vicinal twofold Heck coupling reactions from 1,2-dibromocyclopentene (1), 1,2-dibromocyclohexene (2), 1,2-diiodocyclopentene (8), 1,2-diiodocyclohexene (9), 1-bromo-2-trifluoromethanesulfonyloxycyclohex-1-ene (11), or 1-chloro-2-nonafluorobutanesulfonyloxycyclohex-1-ene (19) with alkenes 3, e. g. methyl, tert-butyl, menthyl, ...

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