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Photochemical α‐Cleavage in Pyran‐2‐thione: Generation of Aldehyde–Thioketene and Thioaldehyde–Ketene Photoproducts
Author(s) -
Breda Susana,
Reva Igor D.,
Lapinski Leszek,
Fausto Rui
Publication year - 2005
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.200400539
Subject(s) - ketene , pyran , aldehyde , chemistry , cleavage (geology) , ring (chemistry) , photochemistry , bond cleavage , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , fracture (geology) , composite material
Ring‐opening photoreaction : UV irradiation ( λ >337 nm) of a matrix‐isolated, unstrained six‐membered‐ring thiocarbonyl compound, pyran‐2‐thione, promotes the ring‐opening photoreaction that leads to the cleavage of the CO α‐bond yielding the open‐ring aldehyde–thioketene, which after subsequent rearrangement can be transformed in its isomeric thioaldehyde–ketene (see picture).