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Issue 0, 1986
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Elaboration of α-substituted benzyl alkyl ethers and sulphides by suppression of the Wittig and related rearrangements via complexation to tricarbonylchromium

Abstract

Co-ordination of benzyl alkyl ethers and sulphides to tricarbonylchromium allows α-substitution via the corresponding α-carbanions to be achieved by suppression of the Wittig and related rearrangements. Little stereoselectivity was observed in the α-methylation of tricarbonylchromium complexes of benzyl ethers derived from a variety of chiral alcohols. Excellent stereoselectivities were observed in the mono- and di-methylation reactions of tricarbonyl[o-xylene-α,α′-diyl bis(methyl ether)]chromium where single diastereoisomers of the α-methyl and α,α′-dimethyl complexes were formed. Deprotonation and methylation of tricarbonyl-syn-1-methoxytetralinchromium occurred stereospecifically with complete retention of configuration under conditions where the corresponding anti-complex was inert. On treatment with base tricarbonyl-(3-chloropropyl benzyl ether)chromium cyclises to give tricarbonyl-(2-phenyltetrahydrofuran)chromium. Exposure of arenetricarbonylchromium complexes to air and sunlight quantitatively liberates the free arene.

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Article type: Paper
DOI: 10.1039/P19860001581
Citation: J. Chem. Soc., Perkin Trans. 1, 1986,0, 1581-1589
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    Elaboration of α-substituted benzyl alkyl ethers and sulphides by suppression of the Wittig and related rearrangements via complexation to tricarbonylchromium

    J. Blagg, S. G. Davies, N. J. Holman, C. A. Laughton and B. E. Mobbs, J. Chem. Soc., Perkin Trans. 1, 1986, 0, 1581
    DOI: 10.1039/P19860001581

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