V. Duchenet et al., SYNTHESIS OF THIO-SUBSTITUTED AND SELENO-SUBSTITUTED METHANOANTHRACENES BY WITTIG REARRANGEMENT, Tetrahedron letters, 35(13), 1994, pp. 2005-2008
When 12-cyano-11-thia- (and 11-selena)-9,10-dihydro-9,10-ethanoanthrac
enes were deprotonated at 0-degrees-C, the resulting carbanions underw
ent a Wittig rearrangement. After hydrolysis or alkylation, 9,10-dihyd
ro-9,10-methanoanthracene derivatives were isolated. The first synthes
is of a seleno-cyanohydrine is also described.