Abstract
Several 2-aryl-2-(1-oxo-2,3-dihydro-1H-pyrrolizin-2-yl)acetonitrile derivatives were synthesised by Michael addition of (E)-2-arylidene-2,3-dihydro-1H-pyrrolizin-1-ones with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride in moderate yields. The structures of all of the products were fully characterised by NMR, IR and high-resolution mass spectrometry, together with X-ray crystallographic analysis.
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