58434-29-0Relevant academic research and scientific papers
Carbon-Carbon Bond Scission during the Reactions of Allylic Hydroperoxides with some Transition Metal Compounds. Result Relevant to a Recent Proposal
Courtneidge, John L.
, p. 381 - 383 (2007/10/02)
The proposal that 4-exo closure of an allylic peroxyl radical can account for the titled reactions of pinocarveyl hydroperoxide has been considered in the light of literature data, along with the results of reactions carried out with a range of alternative copper and iron reagents and with the previously examinated reagents in the presence or absence of suitable traps: an acid-catalysed pathway is proposed to account for the observed scission reaction.
Photooxygenation of olefins in the presence of titanium(IV) catalyst: A convenient 'one-pot' synthesis of epoxy alcohols
Adam,Braun,Griesbeck,Lucchini,Staab,Will
, p. 203 - 212 (2007/10/02)
The photooxygenation of olefins in the presence of transition-metal complexes derived from Ti, V, and Mo constitutes a convenient and efficient 'one-pot' synthesis of epoxy alcohols. First, singlet oxygen transforms the olefin via an ene reaction into its allylic hydroperoxide, and subsequently, the allylic hydroperoxide is converted via transition-metal-catalyzed oxygen transfer into its epoxy alcohol. From the point of view of the olefinic substrate, the oxygen transfer is intermolecular, one allylic hydroperoxide molecule serving as oxygen donor and the other as oxygen acceptor in the form of its allylic alcohol, the transition metal playing the role of a template for both as in the Sharpless epoxidation. Unlike the latter process, the hydroperoxide donor and the allylic alcohol acceptor are generated in situ and continually consumed via a novel oxygen-transfer chain sequence.
