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Synthesis 1991; 1991(2): 117-122
DOI: 10.1055/s-1991-26393
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Synthesis of 5-Alkylidene-6-(dimethylamino)methyl-1,3-cyclohexadienes from α-Substituted Benzyldimethylammoniomethylides

Yoshio Machida* , Naohiro Shirai, Yoshiro Sato
  • *Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, Japan
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Publication Date:
27 September 2002 (online)

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2-Substituted 5-alkylidene-6-(dimethylamino)methyl-1,3-cyclohexadienes (E)-4 and (Z)-4 were prepared by the reaction of α,4-disubstituted dimethyl[(trimethylsilyl)methyl]benzylammonium iodides 2 with cesium fluoride. Their E-isomers were stable at room temperature and could be used in the Diels-Alder reaction. Some related reactions are also described.