Miller, F. M. (Fred Mathias), 1905-1992
M.S. (Master of Science)
Department of Chemistry
Organonitrogen compounds; Organochlorine compounds
It has been reported that acetamide reacts with 2,3-dimethylbutadiene in the presence of phosphorus oxychloride via the Diels-Alder cycloaddition to afford dihydropyridine derivatives. We have re-examined this reaction and found an unidentified compound which is different from that reported and which can not be confirmed as an adduct from cycloaddition. Both δ-valerolactam and ε-caprolactam were used as precursors for cyclic imidoyl chlorides for use as possible dienophiles in the concerted cyclization. However, all attempts to trap the cyclic imidoyl chloride as a Diels-Alder adduct with either 2,3-dimethylbutadiene or cyclopentadiene failed. Instead, various self-condensation compounds were obtained depending on the inorganic acid chloride employed. From the results obtained in this investigation, we therefore arrive at the conclusion that the instability and high polarization of imidoyl chlorides lead them to react through nucleophilic displacement rather than Diels-Alder addition.
Pan, Wen-Hsiung, "An investigation of imidoyl chlorides as possible dienophiles" (1984). Graduate Research Theses & Dissertations. 1356.
vii, 36 pages
Northern Illinois University
Rights Statement 2
NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.