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Synthesis 1991; 1991(11): 1029-1038
DOI: 10.1055/s-1991-26640
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Allenol Ether Intermediates in the Synthesis of 1,7-Dioxaspiro[5.5]undec-4-enes and 1,6-Dioxaspiro[4.5]dec-3-enes

Philip Kocieński* , Richard Whitby
  • *Department of Chemistry, The University, Southampton, SO9 5NH, England
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Publication Date:
29 April 2002 (online)

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Sequential dialkylation of methoxyallene via the corresponding lithium derivatives gives 1,3-dialkylated methoxyallenes which undergo acid-catalysed ring closure to 1,7-dioxaspiro[5.5]undec-4-enes. Similarly, cyclic allenol ethers (2-vinylidenetetrahydropyrans) generated by rearrangement of 2-alkynyltetrahydropyrans cyclise on treatment with acid to give 1, 6-dioxaspiro[4.5]dec-3-enes.