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1985•Chemistry LettersRequires access

THE PRINS-TYPE REACTIONS OF MONO- AND 1,1-DISUBSTITUTED ALKENES WITH TRICHLOROACETONITRILE IN THE PRESENCE OF BORON TRICHLORIDE

Hiroshi Hamana, Tsutomu Sugasawa

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Abstract

Abstract Boron trichloride was found to be a useful Lewis acid for the Prins-type reaction of alkenes with electron-deficient nitriles. In its presence, monosubstituted alkenes react with trichloroacetonitrile, giving dichloroazirine derivatives in high yields. Further exposure of the azirine derivative to boron trichloride at room temperature afforded α,α,γ-trichloroalkylnitrile. The Prins-type acylations of 1,1-disubstituted alkenes with trichloroacetonitrile are also described.

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Abstract Boron trichloride was found to be a useful Lewis acid for the Prins-type reaction of alkenes with electron-deficient nitriles. In its presence, monosubstituted alkenes react with trichloroacetonitrile, giving dichloroazirine derivatives in high yields. Further exposure of the azirine derivative to boron trichloride at room temperature afforded α,α,γ-trichloroalkylnitrile. The Prins-type acylations of 1,1-disubstituted alkenes with trichloroacetonitrile are also described.

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Available abstract

Abstract Boron trichloride was found to be a useful Lewis acid for the Prins-type reaction of alkenes with electron-deficient nitriles. In its presence, monosubstituted alkenes react with trichloroacetonitrile, giving dichloroazirine derivatives in high yields. Further exposure of the azirine derivative to boron trichloride at room temperature afforded α,α,γ-trichloroalkylnitrile. The Prins-type acylations of 1,1-disubstituted alkenes with trichloroacetonitrile are also described.

Key concepts: Chemistry, Boron trichloride, Boron, Medicinal chemistry, Organic chemistry

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THE PRINS-TYPE REACTIONS OF MONO- AND 1,1-DISUBSTITUTED ALKENES WITH TRICHLOROACETONITRILE IN THE PRESENCE OF BORON TRICHLORIDE — Research Paper | ScholarLens