allyl acetate was developed by the use of [Ir(cod)2]+BF4- complex. For instance, the reaction of allyl acetate with n-octyl alcohol in the presence of a catalytic amount of [Ir(cod)2]+BF4- complex afforded allyl octyl ether in quantitative yield. Allyl carboxylates were also prepared by the exchange reaction between carboxylic acids and allyl acetate in good yields. The [Ir(cod)2]+BF4- complex catalyzed
Facile O-Deallylation of Allyl Ethers via S<sub>N</sub>2‘ Reaction with <i>tert</i>-Butyllithium
作者:William F. Bailey、Michael D. England、Michael J. Mealy、Charnsak Thongsornkleeb、Lisa Teng
DOI:10.1021/ol991342g
日期:2000.2.1
[reaction: see text] Allylic ethers are converted to the corresponding alcohol or phenol in virtually quantitative yield at temperatures below ambient simply by stirring a hydrocarbon solution of the ether with 1 molar equiv of tert-butyllithium. The reaction, which produces 4,4-dimethyl-1-pentene as a coproduct, most likely involves an S(N)2' attack of the organolithium on the allyl ether.
An allyl-containing compound represented by following Formula (3):
wherein R2, R3, R4, R5 and R6 may be the same as or different from one another and each represent hydrogen atom or an organic group; R7 represents an organic group; and Y represents oxygen atom or sulfur atom, is produced by reacting an allyl ester compound represented by following Formula (1):
wherein R1 represents hydrogen atom or an organic group; and R2, R3, R4, R5 and R6 are as defined above, with a compound represented by following Formula (2):
R7-Y-H (2)
wherein R7 is an organic group; and Y is as defined above, in the presence of at least one transition element compound.