CHIN-HUNG LAI2026-10-162026-10-162023-03-01Pure ID: 15096893Pure UUID: a553cbb7-4cfc-4cdc-a2d8-59934ab8ba2f10.1002/poc.4466https://www.scopus.com/pages/publications/85142881284https://scholars.csmu.edu.tw/handle/123456789/30115In this study, we attempted to explain why the substitution of a cyano group onto the 1-azadiene moiety promotes N-(2,3-diphenylallylidene)pent-4-en-1-amine to undergo an intramolecular aza-Diels–Alder reaction. Our M06-2X study found that the intramolecular aza-Diels–Alder reaction of N-(2,3-diphenylallylidene)pent-4-en-1-amine has an inverse electron demand. Therefore, the attachment of a cyano group to the diene moiety (1-azadiene) makes the intramolecular aza-Diels–Alder reaction feasible. Moreover, the intramolecular aza-Diels–Alder reaction of N-(2,3-diphenylallylidene)pent-4-en-1-amine was found to be a kinetically controlled reaction.enjournal article