ON THE DIRECT METALATION OF ISOPRENE

Article abstract of DOI:10.1016/S0040-4020(01)96114-9

Isoprene has been metalated in tetrahydrofuran with an excess of sterically hindered potassium dialkylamides, prepared by combining equimolar amounts of the corresponding lithium amide and potassium tert-butoxide.Subsequent reaction with oxirane, alkyl bromides, and pivaldehyde gave the expected coupling products in reasonable yields.Coupling with (CH3)2CHCH2CH=O and (CH3)2C=CHCH=O afforded the bark beetle pheromones (+/-)-ipsenol and (+/-)-ipsdienol in low yields.