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Issue 18, 2019
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Allylic azides: synthesis, reactivity, and the Winstein rearrangement

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Organic azides are useful synthetic intermediates, which demonstrate broad reactivity. Unlike most organic azides, allylic azides can spontaneously rearrange to form a mixture of isomers. This rearrangement has been named the Winstein rearrangement. Using allylic azides can result in low yields and azide racemization in some synthetic contexts due to the Winstein rearrangement. Effort has been made to understand the mechanism of the Winstein rearrangement and to take advantage of this process. Several guiding principles can be used to identify which azides will produce a mixture of isomers and which will resist rearrangement. Selective reaction conditions can be used to differentiate the azide isomers in a dynamic manner. This review covers all aspects of allylic azides including their synthesis, their reactivity, the mechanism of the Winstein rearrangement, and reactions that can selectively elaborate an azide isomer. This review covers the literature from Winstein's initial report to early 2019.

Graphical abstract: Allylic azides: synthesis, reactivity, and the Winstein rearrangement

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Publication details

The article was received on 21 Dec 2018, accepted on 04 Apr 2019 and first published on 04 Apr 2019

Article type: Review Article
DOI: 10.1039/C8OB03178A
Org. Biomol. Chem., 2019,17, 4406-4429

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    Allylic azides: synthesis, reactivity, and the Winstein rearrangement

    A. S. Carlson and J. J. Topczewski, Org. Biomol. Chem., 2019, 17, 4406
    DOI: 10.1039/C8OB03178A

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