1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane (4) reacted with alkyl halides to give the alkylated cyclopropyl sulfones 6, which were subjected to hydrolysis with TiCl4in CH2Cl2followed by elimination of the phenylsulfonyl group with DBU to afford α,β-unsaturated esters 8 and small amount of...
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th-mahidol.225422018-08-10T16:01:16Z 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. Manat Pohmakotr Jantima Ratchataphusit Mahidol University Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane (4) reacted with alkyl halides to give the alkylated cyclopropyl sulfones 6, which were subjected to hydrolysis with TiCl4in CH2Cl2followed by elimination of the phenylsulfonyl group with DBU to afford α,β-unsaturated esters 8 and small amount of β,γ-unsaturated esters 9. Furthermore, reductive removal of the phenylsulfonyl group of compound 6 by using 6% Na-Hg furnished 2-alkyl substituted cyclopropanone acetals 12 in good yields. © 1993. 2018-08-10T08:54:16Z 2018-08-10T08:54:16Z 1993-01-01 Article Tetrahedron. Vol.49, No.29 (1993), 6473-6482 10.1016/S0040-4020(01)80161-7 00404020 2-s2.0-0027328990 https://repository.li.mahidol.ac.th/handle/123456789/22542 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0027328990&origin=inward |
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Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics Manat Pohmakotr Jantima Ratchataphusit 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. |
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1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane (4) reacted with alkyl halides to give the alkylated cyclopropyl sulfones 6, which were subjected to hydrolysis with TiCl4in CH2Cl2followed by elimination of the phenylsulfonyl group with DBU to afford α,β-unsaturated esters 8 and small amount of β,γ-unsaturated esters 9. Furthermore, reductive removal of the phenylsulfonyl group of compound 6 by using 6% Na-Hg furnished 2-alkyl substituted cyclopropanone acetals 12 in good yields. © 1993. |
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Mahidol University |
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Mahidol University Manat Pohmakotr Jantima Ratchataphusit |
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Manat Pohmakotr Jantima Ratchataphusit |
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Manat Pohmakotr |
title |
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. |
title_short |
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. |
title_full |
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. |
title_fullStr |
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. |
title_full_unstemmed |
1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. |
title_sort |
1-lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons. |
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2018 |
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https://repository.li.mahidol.ac.th/handle/123456789/22542 |
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