AN UNEXPECTED OXYGEN EXTRUSION IN ARYNE-FURAN DIELS-ALDER REACTIONS.

David H. Blank and Gordon W. Gribble*, Department of Chemistry, Dartmouth College, Hanover, NH 03755

The Diels-Alder reaction between furan and benzyne, generated from bromofluorobenzene and magnesium, gives a mixture of the reported adduct: 1,4-dihydro-1,4-epoxynaphthalene (1) and, surprisingly, naphthalene (2). This is unexpected outside the realm of hetarynes. The scope of this reaction and mechanistic implications will be presented.