Strained to the limit: when a cyclobutyl moiety becomes a thermodynamic sink in a protolytic ring-opening of photogenerated oxetanes.
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.
Valiulin
Roman A
RA
Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80208, USA.
Arisco
Teresa M
TM
Kutateladze
Andrei G
AG
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
D002728:Chlorohydrins; D003512:Cyclohexanones; D006576:Heterocyclic Compounds, 4 or More Rings; D011084:Polycyclic Aromatic Hydrocarbons; C028215:2-cyclohexen-1-one