1,7-Dioxa[7](2,7)pyrenophane: The Pyrene Moiety Is More Bent than That of C70

Abstract

The most distorted pyrene moiety yet prepared (see picture) has been synthesized by the valence isomerization of a tethered [2.2]metacyclophane-1,9-diene to a 10b,10c-dihydropyrene and in situ dehydrogenation by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) at 80 °C. The end-to-end bend of the pyrene moiety exceeds that of the corresponding part of the equator of D5h C70.