1793-98-2Relevant academic research and scientific papers
Intramolecular Addition of Alkoxy Radicals. Part 4. Reductive Cyclisation of Olefinic Hydroperoxides
Taillez, Bernard,Bertrand, Michele Paula,Surzur, Jean-Marie
, p. 547 - 554 (2007/10/02)
Pent-4-enyl hydroperoxide reacts with reducing salts (FeX2, TiCl3) to afford tetrahydrofurfuryl compounds (halides or dimers) in high yield from the selective cyclisation of the pent-4-enyloxy radical.Analogous behaviour is observed for photolysis although the yields of cyclic products are lower.The photolysis of hex-5-enyl hydroperoxide does not yield cyclic products but these are observed when this hydroperoxide is reduced by FeCl2.It is suggested that metallic salts are able to complex the alkoxyl radicals thereby making them more electrophilic and hence more prone to cyclise.
