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A new method for the synthesis of mixed orthoesters from O-allyl acetals |
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| Authors: | Stanis?aw Krompiec Robert Penczek Ewelina Kubik Mateusz Penkala Nikodem Ku?nik |
| Institution: | a Institute of Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia ul. Szkolna 9, 40-007 Katowice, Poland b Faculty of Chemistry, Silesian University of Technology, ul. B. Krzywoustego 4, 44-100 Gliwice, Poland c Faculty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznań, Poland |
| Abstract: | Two new methods for the synthesis of orthoesters and compounds containing an orthoester moiety (dihydroisoxazoles) are presented. Mixed orthoesters of general formulas RC(OR1)(OR2)2 and RC(OR1)(OR2)(OR3) were prepared via addition of ROH (R = Bu or m-methylphenyl) to O-allyl acetals (acrolein acetals: diethyl or cyclic, i.e., 2-vinyl-1,3-dioxanes or dioxolanes). The catalytic systems for these reactions were generated from RuCl2(PPh3)3] and Na2CO3; {RuCl2(COD)]x} or {OsCl2(1,5-COD)]x}, PPh3, and Na2CO3. Compounds containing an orthoester moiety (dihydroisoxazoles) were prepared via tandem isomerization of O-allyl acetals (to O-vinyl acetals) catalyzed by ruthenium complexes followed by cycloaddition to in situ-generated 2,6-dichlorophenylnitrile oxide. |
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