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Photochemical isomerization of pentaatomic heterocycles
This chapter focuses on the photochemical isomerization of penta-atomic heterocyclic compounds. The description of the photochemical behavior of pentaatomic heterocyclic compounds is confused. Five mechanisms are invoked to justify the observed behaviors: (1) the ring contraction-ring expansion route (RCRE), (2) the internal cyclization-isomerization route (ICI), (3) the van Tamelen-Whitesides general mechanism (VTW), (4) the Zwitterion-tricycle route (ZT), (5) the fragmentation-readdition route (FR). The direct irradiation of a penta-atomic heterocycle leads to the formation of a singlet-excited state. This excited state can interconvert into the corresponding triplet state or into the corresponding Dewar isomer. The Dewar isomer is the origin of the formation of isomeric heterocyclic derivatives. The excited triplet state obtained via intersystem crossing from the corresponding excited singlet state or via a sensitized reaction can evolve to give a biradical intermediate. This biradical intermediate can be converted into decomposition products or into ring-contraction products. The ring-contraction products can be irradiated under the reaction conditions used to give isomeric heterocyclic derivatives.
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Reference£º
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com