406486-82-6Relevant academic research and scientific papers
Oxonia-Cope rearrangement and side-chain exchange in the Prins cyclization
Crosby, Stuart R.,Harding, John R.,King, Clare D.,Parker, Gregory D.,Willis, Christine L.
, p. 577 - 580 (2007/10/03)
(Formula Presented) TMSOAc OAc OAc 2 3 Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.
