Abstract
| - Solid-state photoreactions of S-(o-tolyl), S-phenyl, and S-(m-tolyl) 2-benzoylbenzothioates, whichformed chiral crystals by spontaneous resolution, underwent an unprecedented intramolecular cyclizationinvolving phenyl migration to afford optically active corresponding 3-phenyl-3-(arylthio)phthalide in goodchemo- and enantioselectivities. Stereochemical assignment and substituent probe experiment of thisphotoreaction sequence led to a reliable conclusion that this reaction was rationalized on the basis of the arylmigration rather than the well-recognized radicalic mechanism. Furthermore, the chirality preservation in thecrystals was demonstrated by means of the bisignated CD spectra, which allowed assignment of the origin ofthe specific CD band and the helicity of the chiral molecules.
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