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1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.

8

Issued Date

1993-01-01

Resource Type

Article

ISSN

00404020

DOI

10.1016/S0040-4020(01)80161-7

Other identifier(s)

2-s2.0-0027328990

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron. Vol.49, No.29 (1993), 6473-6482

Suggested Citation

Manat Pohmakotr, Jantima Ratchataphusit 1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.. Tetrahedron. Vol.49, No.29 (1993), 6473-6482. doi:10.1016/S0040-4020(01)80161-7 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/22542

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Title

1-Lithio-2,2-diphenoxy-1-(phenylsulfonyl)cyclopropane as β-lithio acrylate and cyclopropanone acetal anion synthons.

Author(s)

Manat Pohmakotr
 Jantima Ratchataphusit

Other Contributor(s)

Mahidol University

Abstract

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.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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https://repository.li.mahidol.ac.th/handle/123456789/22542

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Scopus 1991-2000