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

Michael J. Gallagher, Stephen Harvey, Colin L. Raston, Rodney E. Sue

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

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).

Original languageEnglish
Pages (from-to)289-290
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number4
DOIs
Publication statusPublished - 15 Feb 1988
Externally publishedYes

Fingerprint Dive into the research topics of 'Benzylic Grignard reagents: Application of [Mg(anthracene)(thf) <sub>3</sub>] (thf = tetrahydrofuran) in regioselective Grignard formation and C-O cleavage in benzyl ethers'. Together they form a unique fingerprint.

Cite this