期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 10, 期 39, 页码 7928-7932出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob26528a
关键词
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资金
- MICINN [CTQ-2010-14882, CTQ-2009-13699, JCI-2010-06204]
- Generalitat Valenciana [Prometeo 2008/90]
- CSIC [JAEDOC 101-2011]
- UPV [20100994]
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.
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