Journal of Organic Chemistry p. 4894 - 4899 (1984)
Update date:2022-08-05
Topics:
Wenkert, Ernest
Michelotti, Enrique L.
Swindell, Charles S.
Tingoli, Marco
The substitution of alkoxy groups of enol ethers (1-methoxycyclohexenes, 1-methoxy-1-alkenes, and benzofuran) and aryl ethers (methoxynaphthalenes, cresyl methyl ethers, and dimethoxybenzenes) by hydrogen, alkyl groups, and aryl units, through Grignard reactions catalyzed by bis(triphenylphosphine)nickel dichloride or <1,3-bis(diphenylphosphino)propane>nickel dichloride, is described.The stereochemistry of the new reaction is portrayed, especially in connection with processes involving ring opening of dihydropyrans and dihydrofurans.The reaction has been applied to the synthesis of a termite trail pheromone and the acetate of the Douglas fir beetle aggregation pheromone.
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