Tributyltin Hydride (Bu₃SnH)

Experimental and theoretical studies of the [3,3]-sigmatropic rearrangement of prenyl azides

“…39 These authors proposed a S N 2 0 with the azide attacking the terminal olenic carbon and releasing a TMSO as possible mechanism for that reaction. Different authors have also reported the same results using substituted phenyl propenols, 16,21,23,40 and different reagents and reaction conditions. The reaction of homoallylic alcohols using TMSN 3 under PdCl 2 catalysis also produced the conjugated products.…”

“…In recent years, numerous methods for the preparation of allylic azides by substitution reactions from allylic halides or (homo)allylic alcohols and metal-catalysed azidation have been reported. [15][16][17][18][19][20][21][22][23] However, allylic halides are very reactive species and are prone to decomposition. On the other hand, metal-catalysed reactions are very expensive.…”

“…Also, in different reported procedures to generate 6b the same regioisomer proportions were obtained, regardless of reaction conditions used (temperature, solvents, reagents, catalysts). 16,21,33,34 These results demonstrate that isoprenyl azides cannot be obtained as pure isomer and consequently not requiring regiopure isoprenols for their preparation, which results in a signicant cost reduction. The relative tertiary azide proportion increases 15% ( Fig.…”