Reaction of β-, γ-, and δ-chloroalkanamides with potassium tert-butoxide in tetrahydrofuran: Elimination, and lactamization

Article abstract of DOI:10.3987/COM-97-8061

γ- and δ-Chloroalkanamides were found to undergo lactamization readily when treated with potassium tert-butoxide in tetrahydrofuran. Raising the reaction temperature may encourage S_N2 displacement reaction. On the other hand β-chloroalkanamides only undergo elimination, followed by dimerization and trimerization of the acrylamide initially formed.