CHEMISTRY OF ISODRIN DERIVATIVES - THE SYNTHESES OF 0-HEXAHYDRO-ENDO,ENDO-1,4-9,10-DIMETHANOANTHRACENE AND 0-HEXAHYDRO-ENDO,ENDO-1,4-9,10-DIMETHANOANTHRACENE

The titled compounds are synthesized through multi-step sequences invo lving consecutive [(pi)4(s) + (pi)2(s)] cycloadditions of norbornadien e with two units of chlorinated cyclopentadiene. A dyotropic double hy drogen migration was observed between two closely located double bonds during the process of aromatization of a cyclohexadiene moiety. A hyd roxyl group is introduced onto either of the two methylene bridges in order to provide products suitable for solvolytic analyses.