Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
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Royal Society of Chemistry
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[3,3]-Sigmatropic rearrangement of isoprenyl azides has been extensively investigated in an experimental
and theoretical level. Prenylazides with different chain lengths and phenyl prenylazide have been
synthesized. NMR analysis of each azide has been made to determine the equilibrium composition,
showing the predominance of primary allyl azides over the tertiary ones and E over Z isomer, regardless
of the chain length, temperature, solvent or the regiochemistry of the precursor isoprenyl alcohol. It was
determined that phenyl prenylazides do not experience [3,3]-sigmatropic rearrangement. In order to
rationalize the experimental results and to gain insight in the mechanism of the [3,3]-sigmatropic
rearrangement of prenylazides a theoretical study was performed using density functional theory and the
QTAIM approach.
This is a post-peer-review, pre-copyedit version of an article published in RSC Advances. The final authenticated version is available online at: https://doi.org/10.1039/c7ra09759j
This is a post-peer-review, pre-copyedit version of an article published in RSC Advances. The final authenticated version is available online at: https://doi.org/10.1039/c7ra09759j
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