Abstract
1 (R), 4 (R)-(-)-1, 4-Diphenyl-2-butyn-1, 4-diol (IIIb) was obtained accompanying with the meso-diol (IIIa) by Grignard reaction of (R)-(-)-1-phenyl-2-propyn-1-ol and benzaldehyde. Each of diasteroisomers was oxidized with manganese dioxide to the same 1, 4-diphenyl-2-butyn-1, 4-dione. The levorotatory glycol (IIIb) was derived to the corresponding diacetate V, which was oxidized with aqueous potassium permanganate into O-acetyl-(S)-(+)-mandelic acid (VI) and the absolute configuration of IIIb was further confirmed as (R) -system. 1 (S), 4 (S)-(+)-1, 4-Diphenyl-2-butyn-1, 4-diol (IIIc) was similarly obtained from (S)-(+)-1-phenyl-2-propyn-1-ol and benzaldehyde. A stoichiometric mixture of the enantiomorphs (IIIb and IIIc) gave the racemic compound IV melted at 101∼102°.
