Journal of Organic Chemistry p. 2101 - 2108 (1982)
Update date:2022-08-05
Topics:
Winkle, Mark R.
Ronald, Robert C.
The methoxymethoxy substituent acts as a relatively strong ortho-directing group in hydrogen-metal exchange reactions.However, the directing effects are influenced by the metalation medium, thus permitting an unusual degree of control of the site of metalation.In conjunction with weak ortho-directing groups, the metalation ortho to the methoxymethoxy group can be directed to either of the ortho positions by controlling the electron-donating capacity of the metalating solvent.In strongly donating solvents the 1,2,4-substitution pattern will arise from a meta-substituted methoxymethoxy arene, while in nondonating solvents the 1,2,3-substitution is favored.In addition, the methoxymethoxy group serves also to enhance the rate of metalation and to stabilize the aryl-metalated products so that some competing addition reactions are supressed.
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