Chiral crystals of the achiral 0x0 amide N,N-di-isopropylphenylglyoxylamide, prepared in large quantities, were irradiated in the solid state to give the optically active B-lactam 3-hydroxy-1 -isopropyl-4,4-dimethyl-3-phenylazetidin-2-one in high optical and chemical yields.

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Phthalimides which have a chiral alkyl group on the nitrogen atom, and which can easily be derived from potassium phthalimide and a chiral alkyl halide, were resolved by complexation with an optically active host compound. Decomposition, with hydrazine, of the resolved phthalimides gave optically active amines. Chiral recognition in an inclusion crystal of optically active N-azetidinone-substituted phthalimide and the optically active 10,l O'-dihydroxy-9,9'-biphenanthryl host compound was studied by X-ray structure analysis.

Reaction of 1,2,3-triarylbenzo[b]thiophenium salts with alkoxide anions results in the exclusive formation of (2) alkoxy-substituted alkenes, indicating that the nucleophilic ring-opening reaction proceeds with complete retention of configuration.

Reactions of 1-arylbenzo[b]thiophenium salts with methoxide anion in methanol caused the fission of the S+-C(2) bond of the thiophenium ring to produce o-(phenylthio)phenyl-substituted methoxyethenes, allenes, or alkynes.