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Paper | Regular issue | Vol 48, No. 3, 1998, pp.481-489
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8061
Reaction of β-, γ-, and δ-Chloroalkanamides with Potassium tert-Butoxide in Tetrahydrofuran: Elimination, and Lactamization

Eng Chi Wang* and Huey-Jen Lin

*School of Chemistry, Kaohsiung Medical University, 100 Shin Chuen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.


γ-and δ-Chloroalkanamides were found to undergo lactamization readily when treated with potassium tert-butoxide in tetrahydrofuran. Raising the reaction temperature may encourage SN2-displacement reaction. On the other hand β-chloroalkanamides only undergo elimination, followed by dimerization and trimerization of the acrylamide initially formed.