title: Strained to the limit: when a cyclobutyl moiety becomes a thermodynamic sink in a protolytic ring-opening of photogenerated oxetanes.
abstract: Strained polycyclic oxetanes generated photochemically from the Diels-Alder adducts of cyclic dienes and enones undergo deep skeletal rearrangements under protolytic ring-opening conditions offering expeditious access to chlorohydrins and other products of unique skeletal topology.
authors.affiliation: Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80208, USA.
authors.forename: Roman A
authors.initials: RA
authors.lastname: Valiulin
authors.forename: Teresa M
authors.initials: TM
authors.lastname: Arisco
authors.forename: Andrei G
authors.initials: AG
authors.lastname: Kutateladze
mesh_terms: D002384:Catalysis; D002728:Chlorohydrins / Q000138:chemical synthesis* / Q000737:chemistry; D003512:Cyclohexanones / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D002728:Chlorohydrins; D003512:Cyclohexanones; D006576:Heterocyclic Compounds, 4 or More Rings; D011084:Polycyclic Aromatic Hydrocarbons; C028215:2-cyclohexen-1-one