Stereochemical relations in the bornane series : An example of preferred exo attack

Abstract

The four α-hydroxybornanones have been obtained as their crystalline p-chlorobenzoates; the two endo ketoesters via photochemical reaction of camphorquinone and p-chlorobenzaldehyde and the two exo-isomers from cis, exo-bornanediol. cis-Diols were produced in every case by reaction of these ketoersters with p-methylbenzyl magnesium chloride, the endo-ketoesters affording cis, endo-diols via exo attack of the Grignard reagent on the bornane system. Two of the possible trans-diols were also synthesized.