A General Method for the Synthesis of 2-Alkyl Substituted 1,3-Dienes Starting from 2-(Chloromethyl)-3-tosylpropene

Article abstract of DOI:10.1016/S0040-4020(01)85650-7

The alkylation of the monolithium derivative 5 of 2-(chloromethyl)-3-tosylpropene (1) with bromo- or iodo-methyltrimethylsilane affords the β-silyl sulfone 7, which after nucleophilic substitution of the chlorine atom followed by β-elimination of tosyltrimethylsilane, promoted by tetrabutylammonium fluoride (TBAF), gives 2-substituted conjugated dienes 6 and the outer-ring diene 14.Racemic ipsenol (10b), an aggregation pheromone of the bark beetle Ips paraconfusus Lanier, is prepared.