Zur Borylierung von Benzol und Naphthalin durch Dehalogenierungsprodukte von Dichlor(diisopropylamino)boran☆

Add time:08/19/2019    Source:sciencedirect.com

The formation of the compounds C6H6 · xBN(i-C3H7)2 (x = 1–6) from the reaction of dichloro(diisopropylamino)borane with sodium/potassium alloy in 1,2-dimethoxyethane, has been confirmed by mass spectrometric studies (high resolution, field ionisation and collision activation using “linked scan” analysis). The compounds with x = 2 and x = 3 were separated from the reaction mixture and identified as compounds C6H6 · 2BN(i-C3H7)2 (Ia) and C6H6 · 3BN(i-C3H7)2 (II) by NMR (1H, 11B, 13C and 15N). Hydrolysis of the naphthalene derivative, C10H8·2BN(i-C3H7)2 (III) in alkaline medium gives 1-methyl-2-propene-1-yl-benzene (IV) and 1-allyl-2-methylbenzene (V), which suggests that this moiety has structure IIIb (2,10-bis(diisopropylamino)-1,5-dihydro-1,5-epiborano-benzo[c]borepin) rather than that of isomeric IIIa (1,2-bis(diisopropylamino)-1,1a,2,8b-tetrahydro-borireno[2,3-b][3]benzoborepin).

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