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DOI: 10.1055/sos-SD-035-00250

Rück-Braun, K.; Freysoldt, T.Science of Synthesis, (200735275.

General Introduction

Ring opening of aziridines under various conditions leads to the formation of (2-chloroalkyl)amines. These compounds are important synthetic intermediates, and the ring opening can be achieved with a variety of chlorinating reagents. A careful choice of substrate, reaction conditions, and reagents is necessary, as acidic conditions or high temperatures may not be tolerated by certain functional groups in more labile substrates. Acidic or neutral conditions are required to achieve ring opening, but excellent stereo- and regioselectivity can be realized with the right substrate. The reaction proceeds mostly via an SN2 mechanism, with attack at the more hindered carbon atom giving products with an anti configuration. Electron-withdrawing groups on the nitrogen atom are also known to enhance the ring-opening reaction. Additional information on this topic may be found in HoubenWeyl, Vol.11/2, p247.

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