5455-94-7Relevant articles and documents
Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids
Yates, Peter,Burke, Patrick Michael
, p. 1695 - 1704 (2007/10/02)
Reaction of tetrahydro-2,2,5,5-tetramethyl-3(2H)-furanone (1) with 96 or ca. 100percent sulfuric acid or hot polyphosphoric acid followed by aqueous quenching gave the following products: 2-hydroxy-2,5-dimethyl-4-hexen-3-one (3), 2,4,4-trimethyl-2-cyclopenten-1-one (7), 3,5,5-trimethyl-2-cyclopenten-1-one (8), tetrahydro-2,3,5,5-tetramethylfuran-2,3-diol (11), 2,5-dihydro-3,5,5-trimethyl-2-methylenefuran (17) and its dimer 20, 2,5-dihydro-2,3,5,5-tetramethyl-2-furanol (18), 4-hydroxy-2,4-dimethyl-2-pentenoic acid γ-lactone (22), 2,3,5-trimethyl-2-cyclopenten-1-one (23), and tetramethylfuran (25).In 96percent sulfuric acid the products arise by ring opening, ring opening followed by reclosure to carbocyclic products, methyl migration from C-2 to C-3 to give rearranged furan derivatives, and oxidation.In ca. 100percent sulfuric acid or hot polyphosphoric acid further methyl migrations can occur to give 23 and 25.
Regiocontrolled Hydration of 2-Butyne-1,4-diol Derivatives to Give 4,5-Dihydro-3(2H)-furanones. Practical Synthesis of Bullatenone and Geiparvarin
Saimoto, Hiroyuki,Hiyama, Tamejiro,Nozaki, Hitosi
, p. 4975 - 4977 (2007/10/02)
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Synthesis and biological evaluation of substituted 2,2' oxybis(propionic acid) derivatives and related compounds
Bennett,Houlihan,Mason,Engstrom
, p. 709 - 714 (2007/10/05)
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