Masahiro Horiguchi

Coerced photodimerization reaction in the solid state through amine salt formation

Abstract Photodimerization of fumaric or several γ-form trans -cinnamic acids proceeded successfully in the solid state through amine salt formation with ammonia or some aromatic heterocyclic amines (especially, imidazole). It appears that this success is due to a small size or a planar structure of the amine. A layered or a channel-type clathrate crystal structure was revealed, respectively.

ENANTIOMERIC RESOLUTION OF RACEMIC C2-SYMMETRIC TRANS-2,5-DIMETHYL-2,5-DIPHENYLPYRROLIDINE AND TRANS-2,5-DIMETHYL-2,5-BIS(3-HYDROXYPHENYL)PYRROLIDINE BY A DIASTEREOMER METHOD

The racemic samples of C 2 -symmetric trans-2,5-dimethyl-2,5-diphenylpyrrolidine (trans-2a) and trans-2,5-dimethyl-2,5-bis(3-hydroxy-phenyl)pyrrolidine (trans-2b) have been resolved by the diastereomer method using D- or L-tartaric acid as the resolving agent. The enantiomerically enriched trans-2a and trans-2b could be oxidized with Oxone® to give trans-2,5-dimethyl-2,5-diphenylpyrrolidine-1-oxy (trans-1a) and trans-2,5-dimethyl-2,5-bis(3-hydroxyphenyl)pyrrolidine-1-oxy (trans-1b), respectively.