Deprotonation from an N-Methyl Group in 2-[1-(Dimethylamino)-1-methylethyl]phenylborane Derivatives

Reaction of 2-[1-(dimethylamino)-1-methylethyl]phenyllithium (Ar*Li) with a trialkyl borate, B(OR)3, in the 3:1 ratio gave 1-Ar*-3,4,4-trimethyl-1,2,3,4-tetrahydro-3,1-benzazaborin as a major product together with the corresponding protonated compound and the boronic acid. The structure of the hetel...

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Bibliographic Details
Published in:Organometallics 2000-01, Vol.19 (2), p.206-208
Main Authors: Asakura, Mitsuhiro, Ōki, Michinori, Toyota, Shinji
Format: Article
Language:English
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Summary:Reaction of 2-[1-(dimethylamino)-1-methylethyl]phenyllithium (Ar*Li) with a trialkyl borate, B(OR)3, in the 3:1 ratio gave 1-Ar*-3,4,4-trimethyl-1,2,3,4-tetrahydro-3,1-benzazaborin as a major product together with the corresponding protonated compound and the boronic acid. The structure of the hetelocyclic compound was determined by X-ray analysis and NMR spectroscopy. This compound is formed via the deprotonation from one of the N-Me groups in Ar*2B(OR) by the remaining Ar*Li followed by the facile intramolecular cyclization between the boron and carbon atoms.
ISSN:0276-7333
1520-6041
DOI:10.1021/om990724n