Search results for "VINYL ETHERS"

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Ring splitting of azetidin-2-ones via radical anions

2012

The radical anions of azetidin-2-ones, generated by UV-irradiation in the presence of triethylamine, undergo ring-splitting via N-C4 or C3-C4 bond breaking, leading to open-chain amides. This reactivity diverges from that found for the neutral excited states, which is characterised by alpha-cleavage. The preference for beta-cleavage is supported by DFT theoretical calculations on the energy barriers associated with the involved transition states. Thus, injection of one electron into the azetidin-2-one moiety constitutes a complementary activation strategy which may be exploited to produce new chemistry.

AnionsAZETIDINESFree RadicalsUltraviolet RaysElectronVINYL ETHERSRing (chemistry)PhotochemistryBiochemistryPolarizable continuum modelchemistry.chemical_compoundN-(ARYLIDENE(OR ALKYLIDENE)AMINO)-2-AZETIDINONESQUIMICA ORGANICAMoietyReactivity (chemistry)BETA-LACTAM RINGPhysical and Theoretical ChemistryTriethylamineDNA PHOTOLYASEMolecular StructureSTEREOCONTROLLED SYNTHESISOrganic ChemistryTransition stateSTEREOSELECTIVE-SYNTHESISchemistryPOLARIZABLE CONTINUUM MODELExcited stateQuantum TheoryPHOTOCHEMICAL-REACTIONSBUILDING-BLOCKS
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