M. Schmittel et al., BENZO[B]FLUORENES FORMED IN THE THERMAL CYCLIZATION OF 3-ENE-1,6-DIYNES, Zeitschrift fur Naturforschung. B, A journal of chemical sciences, 53(9), 1998, pp. 1015-1020
A three-step preparation of the benzofluorene core is presented. The l
ast step involves thermal cyclization of 3-ene-1,6-diyne (7) leading t
o the formation of four benzofluorene derivatives, one of which has be
en investigated by X-ray analysis. The harsh thermal conditions indica
te that the cyclization of 7 might not proceed via a biradical interme
diate as would be anticipated by a mechanistic proposal from Ueda.