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

Abstract

rahydro-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* 2 B(OR) by the remaining Ar*Li followed by the facile intramolecular cyclization between the boron and carbon atoms.

Elucidation of a detection mechanism of a fluorescent sensor based on photo-induced electron transfer for water

“…4a and 5). As with the case of AnBOH reported by Anslyn and Larkin, 18 for TF-2 the interatomic distance between the boron atom and the nitrogen atom is 3.294 Å which is much longer than the normal B-N bond length of 1.57-2.91 Å, 29,30 2)* distance = 2.883 Å) (Fig. 5).…”

“…4a and 5). As with the case of AnBOH reported by Anslyn and Larkin, 18 for TF-2 the interatomic distance between the boron atom and the nitrogen atom is 3.294 Å which is much longer than the normal B–N bond length of 1.57–2.91 Å, 29,30 indicating a lack of B–N bonding. On the other hand, the crystal structure of TF-2 revealed the existence of the intramolecular OH⋯N hydrogen bonding between the hydroxyl group of the B(OH) 2 moiety and the nitrogen atom of the amino moiety (O(2)H(2)⋯N(1) angle = 169°, O(2)⋯N(1) distance = 2.703 Å), that is, the formation of TF-2H (Fig.…”

Crystal structure of aqua-2-(3-aminophenyl)-1,3,2-dioxaborole dihydrate, C12H12BNO3 · 2H2O

“…A search of the Cambridge Structural Database (CSD, version 5.31) [13], revealed that there is no entry so far for an aqua complex of a boronic acid ester. Until now, solid-state structures of aqua-boron complexes have been reported only for triphenylborane derivatives, in particular for tris(pentafluorophenyl)borane [14,15]. The asymmetric unit of the aqua-catecholboronate contains one aqua-boronate and two uncoordinated water molecules (figure, top).…”

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“…151 Reaction of 2-[1-(dimethylamino)-1-methylethyl]phenyllithium with B(O i Pr) 3 affords the heterocyclic borate 1-{[1-dimethylamino)-1-methylethyl]phe-nyl}-3,4,4-trimethyl-1,2,3,4-tetrahydro-3,1-benzaborin (Scheme 4) as the major boron containing product. 152 A range of stable macrocyclic (tetrameric and pentameric) imidazolylboranes have been prepared {(C 2 R 2 N 2 CH)BRA 2 } n (n = 4 or 5) which are interesting as deprotonatation would form a macrocyclic carbene complex, which has subsequent implications for the synthesis of novel metal-carbene complexes. 153 New diazaboroles of the general formula (Z)-R 1 ( t BuNCH = CHNt BuB)C = CR 2 SnMe 3 (R 1 = H, Me or Et; R 2 = Et, Ph, 4-ClC 6 H 4 , 4-BrC 6 H 4 , n-C 4 H 9 or n-C 6 H 13 ) have been formed by the palladium catalysed insertion of the corresponding alkyne (R 1 C•CR 2 ) into the Sn-B bond of 2-stannyl-2,3-dihydro-1H-1,3,2-diazaborole.…”