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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

✍ Scribed by Shengming Ma; Guangwei Wang

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 239 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01207-8

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✦ Synopsis

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.

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## Abstract For Abstract see ChemInform Abstract in Full Text.