Synthesis of vinyl-substituted oxiranes and their transformation to dihydrofurans |
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| Authors: | S V Popkov L V Kovalenko V P Tashchi L Ya Bogel'fer |
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| Institution: | (1) D. I. Mendeleyev University of Chemical Technology of Russia, 9 Miusskaya pl., 125190 Moscow, Russian Federation;(2) Research Institute of Plant Protecting Chemicals, 33 Ugreshskaya ul., 109088 Moscow, Russian Federation |
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| Abstract: | The reaction of dimethylsulfonium methylide with the carbonyl function of 2-arylidene-cyclohexanones obtained from 2-methylcyclohexanone affords the corresponding spirooxiranes. The application of this reaction to 2,2-dimethyl-6-(5-methylfurfurylidene)cyclohexanone and 2,2-dimethyl-6-(5-chlorofurfurylidene)cyclohexanone leads to substituted 4,4-dimethyl-1-furyl-1,-3,4,5,6,7-hexahydroisobenzofurans.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1439–1443, August, 1994. |
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| Keywords: | 2-methylcyclohexanone aromatic and heterocyclic aldehydes Claisen— Schmidt reaction C-methylation Corey— Chaykovsky reaction spirooxiranes substituted hexahydroisobenzofurans |
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