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33.4.14 Product Subclass 14: Alk-1-enyl Azides

DOI: 10.1055/sos-SD-033-00606

Collier, S. J.Science of Synthesis, (200733541.

General Introduction

This section covers the synthesis of alk-1-enyl azides with the generic structure demonstrated by compound 1 (Scheme 1), focusing mainly upon the construction of the eneN3 unit. Previously published information on alkenyl azides can be found in HoubenWeyl, Vol.E 15, p818, and this includes some literature not covered in this section. Alk-1-enyl azides 1 are quite often encountered in organic synthesis and there are many reports detailing their synthesis and reactions. In particular, azidocinnamate derivatives 2 have been widely studied. As such, this section cannot be comprehensive although the most useful approaches to these compounds will be discussed, along with some of the more uncommon syntheses. Detailed discussion of the reactions of these compounds is similarly omitted due to size constraints, but a few representative reactions are given. Key structural data on these compounds includes a strong characteristic absorbance of the azide unit at approximately 2100cm1, and with azidocinnamates the C=C bond can be seen in the region of 1620cm1. As with many organo azides, alkenyl azides are potentially very dangerous, and great care must be taken when handling these compounds, particularly during concentration and physical handling of isolated products due to the explosive potential of the azide function. For example, 3-azidocrotonates are reported to detonate upon contact with sulfuric acid.[‌1‌]

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References


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