Unexpected SN2′-type addition-elimination reactions of 1-aryl-2,3-allenols with LiX. Synthesis and synthetic application of 1-aryl-3-halo-1,3-dienes Article

Jiao, Y, Valente, E, Garner, ST et al. (2002). Unexpected SN2′-type addition-elimination reactions of 1-aryl-2,3-allenols with LiX. Synthesis and synthetic application of 1-aryl-3-halo-1,3-dienes . TETRAHEDRON LETTERS, 43(33), 5723-5726. 10.1016/S0040-4039(02)01207-8

cited authors

  • Jiao, Y; Valente, E; Garner, ST; Wang, X; Yu, H

authors

abstract

  • 1-Aryl-3-halo-1,3-dienes were prepared from the sequential addition-elimination reaction of 1-aryl-2,3-allenols with LiX (X=Br, Cl) in HOAc in moderate to good yields. Here the aromatic substituent is crucial to this interesting transformation since no reaction was observed with 1-alkyl or perfluoroalkyl-2,3-allenols. The 1-aryl-3-halo-1,3-dienes prepared can be used as useful partners in Diels-Alder reactions with dienophiles leading to polycyclic quinone derivatives. © 2002 Elsevier Science Ltd. All rights reserved.

publication date

  • August 12, 2002

published in

Digital Object Identifier (DOI)

start page

  • 5723

end page

  • 5726

volume

  • 43

issue

  • 33