An interesting inclusion phenomenon with (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro[4.4]nonane bromide and (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro[4.5]decane bromide and optical resolution of binaphthyl and biphenanthyl diols by inclusion crystallization with these optically active ammonium salts

Recrystallization of the spiro-pyrrolidinium salts (S)-1-(hydroxydiphenyl methyl)-5-azoniaspiro4.4]nonane bromide or (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro4.5] decane bromide from chloroform afforded a crystalline spiro-pyrrolidinium salt including two molecules of chloroform which was determined by 'H nmr elemental analysis, and X-ray analysis. Racemic 2.2-dihydroxy-1, 1-binaphthyl and 10, 10-dihydroxy-9,9-biphenanthryl have been resolved effectively by inclusion crystallization using these chiral ammonium salts.