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Synthesis 1991; 1991(2): 173-176
DOI: 10.1055/s-1991-26410
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Synthesis of Divinyl-1-oxaspiro[m.4]alkanes and Divinyl-1-oxaspiro[m.4]alkan-2-ols from 1,8-Bis(trimethylsilyl)-2,6-octadiene and Acyl Chlorides

Arlette Tubul* , Philippe Ouvrard, Maurice Santelli
  • *Laboratoire de Synthèse Organique, URA-CNRS 1411, Faculté de St-Jérôme, 13397 Marseille Cedex 13, France
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Publication Date:
27 September 2002 (online)

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Titanium(IV) chloride mediated condensation of 1,8-bis(trimethylsilyl)-2,6-octadiene with α, β, γ or δ-haloacyl chlorides leads to the potentially useful intermediates (d,l)-1-haloalkyl-2,5-divinylcyclopentanols. The latter, under basic treatment, afford divinyl-1-oxaspiro[m.4]alkanes (m = 2-5). Dialkylation of methyl (chloroformyl) alkanoates followed by reduction provides divinyl-1-oxaspiro[m.4]alkan-2-ols (m = 4 and 5).