- Benzylic Grignard Reagents: Application of (thf = tetrahydrofuran) in Regioselective Grignard Formation and C-O Cleavage in Benzyl Ethers
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Benzylic Grignard reagents (2)-(4), bearing ortho- and para-halogeno ring substituents, are readily accessible by treating the corresponding benzylic halide with (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).
- Gallagher, Michael J.,Harvey, Stephen,Raston, Colin L.,Sue, Rodney E.
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p. 289 - 290
(2007/10/02)
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- An Investigation of the Di-Grignard Approach to Metallabenzocyclobutenes of Group 14
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The reactions of 1,2-dihydro-1-magnesabenzocyclobutane (5) with dichlorodimethylsilane (12a), dichloromethylgermane (12b) and dichloromethylstannane (12C) are reported; 1,2-dihydro-1,1-dimethyl-1-silabenzocyclobutene (14a) and 1,2-dihydro-1,1-dimethyl-1-germabenzocyclobutene (14b) were formed in high yields, but the tin analogue was not obtained.Eight-membered ring species, the dimers 17 and 18, were isolated for all three metals.Other products gave useful indications of the probable course of these interesting and complex reactions.
- Boer, H. J. R. De,Akkerman, O. S.,Bickelhaupt, F.
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p. 291 - 306
(2007/10/02)
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