183075-22-1Relevant academic research and scientific papers
Synthesis of 2,3,5-Trisubstituted Furans by the Acid-Catalyzed Decomposition of 1,2-Dioxan-3-ols
Qian, Chang-Yi,Hirose, Jun-ichi,Nishino, Hiroshi,Kurosawa, Kazu
, p. 1219 - 1228 (2007/10/02)
Thirteen new 2,3,5-trisubstituted furans were prepared by the acid-catalyzed decomposition of 6,6-disubstituted 1,2-dioxan-3-ols in 57-93percent yields.The reaction could be accounted for as the consequence of an oxygen-oxygen bond cleavage by acid and the migration of a phenyl group at the C-6 position followed by cyclization and elimination of a phenol.The migratory aptitude was in the order of 4-MeOC6H4- greater than 4-MeO6H4- greater than Ph- = 4-FC6H4- greater than 4-ClC6H4- = 4-BrC6H4- that was found from the competitive phenyl migration in the reaction of 1,2-dioxan-3-ols bearing two different substituents at the C-6 position.
