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Issue 62, 2015
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A new mechanistic insight on β-lactam systems formation from 5-nitroisoxazolidines

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Abstract

DFT calculations at various theory levels unequivocally show that conversion of 5-nitroisoxazolidines into β-lactams does not take place via a ring opening step (as was hitherto suggested), but takes place according to a three-step, domino-type reaction. Quantum-chemical studies do not indicate the existence of an alternative, kinetically allowed reaction mechanism. In addition, it was shown that this mechanism is a general one, and can be related to a wider class of compounds as an interesting alternative to popular synthesis methods of β-lactams.

Graphical abstract: A new mechanistic insight on β-lactam systems formation from 5-nitroisoxazolidines

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Publication details

The article was received on 27 Apr 2015, accepted on 20 May 2015 and first published on 26 May 2015


Article type: Communication
DOI: 10.1039/C5RA07663C
Citation: RSC Adv., 2015,5, 50070-50072

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    A new mechanistic insight on β-lactam systems formation from 5-nitroisoxazolidines

    R. Jasiński, RSC Adv., 2015, 5, 50070
    DOI: 10.1039/C5RA07663C

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