Synthesis and diels-alder reactions of 5,5-dicyanocyclopentadiene: regioselective synthesis of 1,5-disubstituted-1,3-cyclohexadienes |
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| Authors: | Gary I Dmitrienko Marc E Savard Richard W Friesen Mibbo S Thandi |
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| Institution: | Guelph-Waterloo Centre for Graduate Work in Chemistry, Waterloo Campus, Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1 |
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| Abstract: | 5,5-Dicyanocyclopentadiene, readily prepared in three steps from commercially available cis-1,4-dichloro-2-butene, undergoes Diels-Alder reactions with a number of dienophiles to give 5-substituted 7,7-dicyanobicyclo2.2.1]hept-2-enes with high endo-selectivity. The adduct produced with methyl acrylate undergoes base-induced retro-Michael reactions to give 1-carbomethoxy-5-dicyanomethyl-1,3-cyclohexadiene. |
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