The dichotomy between benzene and fulvene formation in palladium-catalyzed domino tricyclizations of 2-bromotetradec-1-ene-7,13-diynes

Schweizer, Stefan, Schelper, Michael, Thies, Claudia, Parsons, Philip J, Noltemeyer, Mathias and Meijere, Armin de (2001) The dichotomy between benzene and fulvene formation in palladium-catalyzed domino tricyclizations of 2-bromotetradec-1-ene-7,13-diynes. Synlett, - (SP ISS). pp. 920-922. ISSN 09365214

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Abstract

2-Bromotetradec-1-ene-7,13-diynes 1, 5, 12 with different substituents at the acetylenic terminus under palladium catalysis have been found to either yield an angularly bisannelated benzene derivative 3 (79%), or fulvene derivatives of type 5 (52-74%) as well as monoannelated fulvenes 13b-e (32-48%). The mechanisms for all three reaction modes most probably involve intramolecular 5-exo-trig carbopalladations of an intermediate 1,3,5-hexatrienyl-6-palladium bromide intermediate.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Philip Parsons
Date Deposited: 06 Feb 2012 18:45
Last Modified: 19 Mar 2012 15:07
URI: http://sro.sussex.ac.uk/id/eprint/18208
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