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Collier, S. J., Science of Synthesis, (2007) 33, 541.
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 ene—N3 unit. Previously published information on alkenyl azides can be found in Houben–Weyl, Vol. E 15, p 818, 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 2100 cm−1, and with azidocinnamates the C=C bond can be seen in the region of 1620 cm−1. 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]
Meeeee 8 Meeeeee Meeeeeeeee ee Meeeeee Meeeee eee Meeeeeeeeeeeee Meeeeeeeeee
Me eee eeeee eeeeee, eee eeeee eeee eeeeeeee e eeeeee eeeeee eee eeeeeee eeeeeeeeeee. Mee eeeeeeeee ee eeeeeeeeeeeeeee eee eeeeeeeeee eeeeeeeeee ee eee eeee eeeeeeeee, eeeee eeeee eeeee eeeeeeeeeee ee eeeeeeeee. Mee ee eee eeee eeeeee eeeeeeeeeeeeeee ee eeeeeee eeeeee ee eeeee eeeeeeeeee eeee 8M-eeeeeeee eee eeeeeeeeeee,[8–88] eeeee-eeeeee eeeeeeeeeee,[88] ee eeeeeeeeee[8,8,8,88,88–88] eeeeeeeeeeeee ee eee eeeee eeeeeeee. Me eee eeeeeeee ee ee eeeeeeeeeee β-eeeeeeeeeee (e.e., eeeeeee ee eeee), eeeeeeeeeee eee eeeeeee eeeeeee eeeeeeeeeee eee eeeeeeeeee.[88,88]
Meee eeeeeeeeeeeeee eeeeeeeeeee, eeee eeeeeeeeeeeee ee eee eeeee eeeee eeee eeee eeeeeeee. Mee eeee eeeeee eeeeeee eeeeeeeeeeeeee ee eee eeeeeeeeee ee e eeeeeee eeee eeee eee eeeeeee eeee eeee, ee eeeeeeeeeee. Meee eeeee ee eeeeee eeeeeeeeee, ee ee e eeeeeee eeeeeeee eeee ee eeee, eee eeeeeeeeeeeee eeeee eeeeeee ee eeeeeeee.[88–88] Meeeeeeeeeeee, eeeeeeeeeeeeeee eeeeeee eeeeee eeeeeee eeeeeeeeeee eeee eeeee eeeeeeeeee eeeeee ee eeee eeeeeeeee eeeeeeee. Meee, eeeeeeee eeeeee eee eeeeeeeee eeeeee eee eeeeeee eeeee eeeeeeeee (eeeeeeeee eeeeeeeeeeeee eee eeeeeee eeeeeeeeeee),[88,88,88,88,88,88,88,88] eeeeeeeee ee eeeeeee eee eeeeeee eeeeeeeeeee ee eeeeeeeeeeeeeee,[88] eeeeeee eeeeeeeeeeee eee eeeeeee eeeeeeeeeeeee,[88,88,88,88–88] eeeeeeeeeeee,[88,88,88,88–88] eeeeeeeeee,[88,88,88] eee 8,8-eeeee-8-eeeeeeeeee[8.8.8]eeee-8,8,8-eeeeeee,[88] eeeeee eee eeeeeee eeeee eeeeeeeeeee,[88] eeeeeeee eeeeee eee eeeeeee eeeee eeeeeeeee,[88,88,88] eee eeeeeeeeeee eeee eeeeeeee eeeee eeeeeeeee eee eeee eeeee.[88] Meeeeeeeeee eeeeeeeeeeeeeeee ee eeee eee[88]eeeeeeeee eee eee[88]eeeeeeeee eee eeee eeee eeeeeeee.[88] Meeeeeeeeeeeeee[88–888] eee eeeeeeeeeeeeee[888–888] eee ee eeee ee eeeeeeeeeeeee ee eee eeeeeeeee ee α-eeeee eeeee, eeeeeeeee eeeeeeeeeeee eeeee. Me eeeee ee eeeeeeee, eeeeeeeeeeeeeee eeee 8M-eeeeeeee eeee eeeeeeeeee[888–888] ee eeeeeeeeeee.[88,88,88,88,888]
Mee eeeee eeee eeeee ee eeeeeeeeeeeeeeee eeeeeeeeee eeee eeeeeee eeee eeeeeeeeee ee eeeeeeeeee, eee eeee e eeeeeee eeeeeeee eeeee ee eeeeeee ee eee eeee eeee ee eee eeeeeeeee, eeeeeeeeeee ee eeee e eeeeeeee eeeeeeeeee (eee eeeeeee ee eeeeeeeeeeee) eee eeeee.[88,888,888] Meee e eeeeeee eeeeeeeeee eeee, eeeeeeeeeee eee eeeeee[888,888] eee eeee eeeeee, eeeeeeeeeeeeeee eee ee eeeeeeee.[888] Meeeeeeee ee eee eeeeeeeeeeeeeeee eeee eeeeeeee eeeeeeee eeeeee eeee ee eeeeeeeee eee eeee eeee ee eeeeeeee eeee eeeeeeeee.[888,888] Meeeeeeee, eeeeeeeee eeee eeeeeeeeeee eeeee eeeeeeeeeeee eeeeeeeeeeeee, eeeee eeeeeee ee eeee eeeeeee-8-eeeee eeeeeeeeeee (e.e., eeeeeeeeeeeeeeeeee).[88,888–888] Meee eeeeee eeeeeee ee eeeeee eeeeeeeee, eee eeeeeeeeeeeee eeeeeee-8-eee ee eeeeeeee-8-eeeeee eeee,[888] eee eeeeeeee eeeeeeee eeeeeeeeeeee eeee eeeeeeeee-8-eeeeee.[888] Meeeeeeeeeeee, eeeeeeee ee eee eeeeeeeeeeee eeeeeeeeeeee eeee eeeeee eee eeee eeeeeeeeee eeee eeeeeee eeee eeeeeeee eeeee eeeeee ee eeee eeeeeeeeee-8-eeee.[888–888] Me e eeeeeee eeeeeeee, eeeeeeeee eeee eeeeee eeeeeeeee eeeee ee eeeeeeeeeeeeee, eeeee eeeee 8-eeeeeeeee-8-eeeeeeeeeeeeee-8-eeee eeee eeeeeeeee eeee eeeeee.[888] Meeee eeee eeeeeee eeeeee eee eeeeeeeeeeeeeeeee eeeeeee 8,8-eeeeeeeeeeeeeee [eeee eeeeeeeeeee eee eee(eeeeeeeeeeeeeeeee) eeeeeee eeee eeeee-eeeee eeeeeeeeeeeeeee[888] ee eee eeeeeeeeeee eeee eeeeeee eeeee eeeeeeeee],[888] eee 8,8-eeeeeeeeeeeeee eee eeeeeeeeeee eeee ee eeeee.[888]
Mee eeeeeeee ee eee eeeeeeeeeeee ee eeeeeeeeeeeeeee ee eeeeeee eeeeeee eeeeeeeee eee eeeee eeeee. Me eee eeeee, e eeeeee eeeee eeeeeeeee ee eee eeeeeeeee eeeeeeeeee MM-8888 (8, Meeeee 8), eee eee eee eeeeeeeee (8 eee 8) eee eeee ee eeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeeeeeee, eeee eeeeeeeeee eeeeeeeeee ee e eeeeeee eeee (ee eeee 8 eee 8, eeeeeeeeeeee).[88] Me eee eeeeee eeeeeee, eee eeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeeeeee (88, Meeeee 8) ee eeeeeeee eeee eee eeeeeeeeeeeeee 8 eee eeeeeeeeee eeee eee eeeeeee eeeeee, ee eeee eee eee eeeeeee eeee ee 8.[88]
Meeeee 8 Meeeee Meeee Meeeeeeee ee MM-8888 Meeee Meeeeee Meeeee[88]
Meeeee 8 Meeee Meeeeeeee ee Meeeeeeeeee Meeee ee Meeeeee Meeee[88]
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[79] | Meeeee, M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[80] | Meeee, M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
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[85] | Meeeeee, M.; Meeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
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[111] | Meeeeeeee, M. M.; Meee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
[112] | Meeeee, M.; Meeeee-Meeee, M.; Meeeeeee, M. M., Meeeeee, (8888), 88. |
[113] | Meeeee, M.; Meeeeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[114] | Meeeeeeee, M. M. M.; Meeee, M. M.; ee Meeee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 88. |
[115] | Meeeee, M.; Meeeeeíe, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[116] | Meeeee, M.; Máeeeee, M.; Meeóe, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[117] | Meeeeeeee, M.; Meeeeee, M. M.; Meeee, M.; Meeeeeeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[118] | Meeeee, M.; Meeeeeíe, M.; Meeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8. |
[119] | Meeeee, M.; Meeeeeee, M. M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[120] | Meeeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[121] | Meeeee, M.; Meeeeeíe, M.; Meeee, M., Meeeeeeee, (8888), 888. |
[122] | Meeeee, M.; Meeeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
[123] | Meee, M.-M.; Mee, M.; Meee, M.-M.; Mee, M.-M.; Mee, M.-M., Meeee. Meeeee., (8888) 88, 8888. |
[124] | Meeeee, M.; Meeeeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[125] | Múeóe, M.; Meáeeee, M.; Meeáee, M.; Meöeee, M.; Meeeeee, M.; Meeáe, M., Mee. M. Mee. Meee., (8888), 8888. |
[126] | Mee, M.; Meee, M.-M., Meeee. Meeeee., (8888) 88, 88. |
[127] | Meeeee, M.; Meeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[128] | Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 88. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 888.