SIMPLE SYNTHESIS OF &β-SILYLOXYACYLCYCLOPROPANES AND THE HOMOALLYL REARRANGEMENT OF CYCLOPROPYLCARBINOLS BY THE ACTION OF TRIMETHYLSILYL HALIDES IN THE PRESENCE OF ZINC HALIDES

Article abstract of DOI:10.1007/BF00958248

The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave β-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones.Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides.The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.