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Synlett 2000; 2000(11): 1697
DOI: 10.1055/s-2000-7939
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Methoxyallene

Robert Pulz*
  • *Institut für Chemie - Organische Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany
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Publication History

Publication Date:
31 December 2000 (online)

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Since the first preparation of methoxyallene (3) by Hoff, Brandsma and Arens in 1968, this compound with cumulated C=C bonds has emerged as a useful and convenient C-3 building block for many transformations in preparative organic chemistry. This donor-substituted, electron-rich allene is easily accessible in high yield by a two step reaction from propargylic alcohol (1) which is methylated with dimethyl sulfate to give propargylic ether 2 followed by isomerisation of 2 with potassium tert-butoxide. The reactivity of 3 is determined by the enol ether functionality leading to electrophilic addition to C-2 or nucleophilic attack at C-1.