475087-03-7Relevant articles and documents
X-Ray and MO analysis of highly stereoselective solid-state photocycloadditions of 2-pyrones with maleimide
Shimo, Tetsuro,Uezono, Takahiro,Obata, Toru,Yasutake, Mikio,Shinmyozu, Teruo,Somekawa, Kenichi
, p. 6111 - 6116 (2002)
Photoirradiations of grinding mixtures of 4-(ω-arylalkyloxy)-6-methyl-2-pyrones 1i-1o and maleimide 2 in the solid state quantitatively gave only a [2+2] cycloadduct 3j with high stereoselectivity. The 1:1 complex crystals 1j·2, and 1a·2, 1b·2, 1c·2, 1d·2, 1g·2, 1h·2 from another 2-pyrones with 2, were characterized by powder X-ray diffraction technique. The crystal formation was remarkably affected by polar and bulky nature of the substituents at the aryl groups. Four kinds of hydrogen bondings by two ground state species for the crystals were quantitatively estimated, and the photoreaction mechanism was analyzed to proceed via some interactions of the singlet excited state of 1 with ground state of 2 by MO transition state calculation.