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The synthesis of broad scope of novel monosubstituted cyclobuteniminium salts derived from aldo-keteniminium salts and acetylene or 1-propyne is described. The reactivity of cyclobuteniminium salts in Diels–Alder reactions has been studied in detail by DFT calculations and by performing competition reaction with cyclobutenone derivatives.
An efficient access to cyclobutanone derivatives has been developed via a ‘one-pot’ [2+2]/[4+2] sequence involving keteniminium and cyclobuteniminium salts as key intermediates. A broad range of novel cyclobuteniminium salts have been prepared via [2+2] cycloaddition of keteniminium salts and alkynes. The resulting [2+2] adducts were then further transformed by Diels–Alder reaction with various dienes...
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