Benzylic Grignard reagents: application of [Mg (anthracene)(thf) 3](thf= tetrahydrofuran) in regioselective Grignard formation and C–O cleavage in benzyl ethers

MJ Gallagher, S Harvey, CL Raston…

Index: Gallagher, Michael J.; Harvey, Stephen; Raston, Colin L.; Sue, Rodney E. Journal of the Chemical Society, Chemical Communications, 1988 , # 4 p. 289 - 290

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Abstract

Benzylic Grignard reagents (2)–(4), bearing ortho-and para-halogeno ring substituents, are readily accessible by treating the corresponding benzylic halide with [Mg (anthracene)(thf) 3](1) in tetrahydrofuran (thf); o-and p-chloromethyl (methoxymethyl) benzenes with (1) rapidly yield 'di-Grignards' whereas the meta-isomer only affords a mono-Grignard'(5), and bis (methoxymethyl) benzenes slowly undergo C–O cleavage,(6).