Journal of the Chemical Society. Perkin transactions II p. 2061 - 2066 (1991)
Update date:2022-07-30
Topics:
Mori, Yukie
Maeda, Koko
2,4,4,6-Tetraphenyl-4H-pyran and -4H-thiopyran exhibited a photochemical colour change in the solid state.On irradiation in solution, 2,4,4,6-tetraphenyl-4H-pyran gave 1,3,5,6-tetraphenyl-2-oxabicyclo<3.1.0>hex-3-ene, while the 4H-thiopyran gave 1,3,5,6-tetraphenyl-2-thiabicyclo<3.1.0>hex-3-ene as an initial photoproduct, followed by further transformation into 2,3,4,6-tetraphenyl-2H-thiopyran. 4-(4-Bromophenyl)-2,4,6-triphenyl-4H-pyran, 4-(4-methylphenyl)-2,4,6-triphenyl-4H-pyran, and 4-(bromophenyl)-2,4,6-triphenyl-4H-thiopyran also showed photochemical colour changes and finally gave both the phenyl-migrated and the (substituted phenyl)-migrated products in comparable yields in each case. 4-Methyl-2,4,6-triphenyl-4H-thiopyran showed no photochemical colour change in the solid state, but in solution it afforded 4-methyl-2,3,6-triphenyl-2H-thiopyran, whose structure was confirmed by X-ray analysis.Based on comparison with the photochemical behaviour of 2,4,4,6-tetraphenyl-1,4-dihydropyridine and 2,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazine, a six-membered ylide was proposed as the coloured photochemical intermediate.
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