1,2-diazetidines

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1,2-diazetidines
1,2-diazetidines
1,2-diazetidines (general formula)
Azetidine
1,2-diazetidine (basic body)
1,2-diazetidin-3-ones
1,2-diazetidin-3-ones
(general formula)
1,2-diazetidin-3-one
1,2-diazetidin-3-one (basic body)

1,2-Diazetidines are saturated heterocyclic organic chemical substances that contain a four-membered ring consisting of two adjacent nitrogen atoms and two carbon atoms. The unsubstituted basic structure, 1,2-diazetidine, has the empirical formula C 2 H 6 N 2 and has not yet been isolated. However, a number of derivatives of 1,2-diazetidine are known.

Manufacturing

Production of substituted 1,2-diazetidines

The [2 + 2] cycloaddition of an electron-rich alkene (e.g. an enol ether or an enamine ) with an azo compound produces the 1,2-diazetidine derivative 1 :

1,2-Diazetidine Derivative Synthesis A.

Preparation of substituted 1,2-diazetidin-3-ones

The cycloaddition of a ketene to an azo compound leads to the 1,2-diazetidin-3-one 2 :

1,2-Diazetidin-3-one derivative synthesis B

Reactivity

Similar to β-lactams, 1,2-diazetidin-3-one 2 reacts with nucleophiles with ring opening, e.g. B. to 3 :

1,2-Diazetidin-3-one derivative ring opening

Individual evidence

  1. ↑ a b c Theophil Eicher , Siegfried Hauptmann , Andreas Speicher: The Chemistry of Heterocycles, Wiley-VCH, 2012, ISBN 978-3-527-32747-8 , pp. 58–59.