Synthesis of 2,3,5-trisubstituted furans by the acid-catalyzed decomposition of 1,2-dioxan-3-ols |
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Authors: | Chang-Yi Qian Jun-Ichi Hirose Hiroshi Nishino Kazu Kurosawa |
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Abstract: | Thirteen new 2,3,5-trisubstituted furans were prepared by the acid-catalyzed decomposition of 6,6-di-substituted 1,2-dioxan-3-ols in 57-93% 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- > 4-MeC6H4- > Ph- = 4-FC6H4- > 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. |
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