Chemistry - A European Journal p. 807 - 816 (1997)
Update date:2022-08-03
Topics:
Schmittel, Michael
Keller, Manfred
Kiau, Susanne
Strittmatter, Marc
If there is an aryl substituent on the acetylene terminus of enyne allenes, then its reaction mode may be changed from the Myers-Saito cyclization to a novel C2-C6 cyclization resulting in a net intramolecular Diels-Alder or ene reaction. As a consequence, the thermal cyclization of readily accessible acyclic enyne allenes can be utilized for the synthesis of complex benzofulvene and benzofluorene derivatives. Kinetic results of the C2-C6 cyclization reaction indicate a two-step reaction pathway with a benzofulvene biradical intermediate.
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