Abstract
Achiral N-methacryloylthiobenzanilide formed ( Z, E)-conformation of the imide moiety and crystallized in a chiral fashion. The solid-state photoreaction gave optically active β-lactam. The dynamic molecular rearrangement for cyclization was elucidated on the basis of direct comparison of the absolute configuration of both the starting material and the photoproduct. Crystal-to-crystal transformation was observed in the photoreaction of the ( E, E)-conformation of N-isopropyl- N-tigloylthiobenzamide, which needs small atomic rearrangement for the cyclization and gave thietane stereo- and chemo-selectively.
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