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Benzoxetes and Benzothietes ¾ Heterocyclic Analogues of Benzocyclobutene

2012

Benzo-condensed four-ring heterocycles, such as benzoxetes 1 and benzothietes 3 represent multi-purpose starting compounds for the preparation of various higher heterocyclic ring systems. The thermal or photochemical valence isomerizations between the benzenoid forms 1,3 and the higher reactive o-quinoid structures 2,4 provide the basis for the synthetic applications. On the other hand, this valence isomerization impedes in particular the generation and storage of 1 because the thermal equilibrium 1 ⇆ 2 is completely on the side of 2. Thus, the number of erroneous or questionable benzoxete structures published to date is surprisingly high. On the contrary, the thermal equilibrium 3 ⇆ 4 is o…

Double bondflash-vacuum-pyrolysisPharmaceutical ScienceReviewring closureAnalytical Chemistrylcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistryBenzocyclobuteneComputational chemistryHeterocyclic CompoundsDrug DiscoveryOrganic chemistryPolycyclic CompoundsPhysical and Theoretical Chemistryring openingcycloadditionchemistry.chemical_classificationThermal equilibriumValence (chemistry)photochemistryFlash vacuum pyrolysisOrganic ChemistryCycloadditionchemistryChemistry (miscellaneous)Molecular MedicineIsomerizationMolecules
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