Summary.
The photoisomerization of 4,4-dialkyl-2,6-diphenyl-4H-thiopyrans and 4-benzyl-2,4,6-triphenyl-4H-thiopyran was investigated and compared with those of the 2,4,4,6-tetraaryl- and 4-alkyl-2,4,6-triaryl-4H-thiopyran analogues reported earlier. Obviously, the alkyl groups at the 4-positions of the 4H-thiopyrans strongly diminish the efficiency of the di-π-methane rearrangement and, contrastingly, a four-electron suprafacial [1,3]-sigmatropic rearrangement is found to be highly efficient.
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Pirelahi, H., Atarodiekashani, A., Seyyedmoossavi, S. et al. Competitive Photochemical Pathways in the Rearrangement of Tetrasubstituted 4H-Thiopyrans. Monatshefte für Chemie 135, 973–978 (2004). https://doi.org/10.1007/s00706-003-0142-x
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DOI: https://doi.org/10.1007/s00706-003-0142-x