(<i>E</i>)-2-Styryl-[1,3,6,2]dioxazaborolane

Thadani, Avinash N.; Batey, Robert A.; Lough, Alan J.; Smil, D.

doi:10.1107/s1600536802001691

Cited by 3 publications

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References 4 publications

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“…The dioxazaborocane moiety comprises two fused ®ve-membered rings, an arrangement that is reported for all structures containing a dioxazaborocane ring system deposited in the Cambridge Structural Database to date (CSD; Version 5.24; Allen, 2002). For the comparison below, structures containing only non-substituted dioxazaborocane ring systems were selected (Rettig & Trotter, 1975;Thadani et al, 2001Thadani et al, , 2002Doidge-Harrison et al, 1998;Caron & Hawkins, 1998;Howie et al, 1997).…”

Section: Commentmentioning

confidence: 99%

2-(6-Bromopyridin-2-yl)-6-methyl-[1,3,6,2]dioxazaborocane, a new stable (pyridin-2-yl)boronic acid derivative

et al. 2004

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The crystal structure of the first reported non‐substituted N‐methyldioxazaborocane confirms that the presence of a methyl group attached to the N atom introduces an NB bond length that is longer than that in a simple dioxazaborocane ring. The presence of more N atoms in the vicinity of the B atom in the title compound [systematic name: 6a‐(6‐bromopyridin‐2‐yl)‐3a‐methyl‐2,3,4,5‐tetrahydro‐1,6‐dioxa‐3a‐aza‐6a‐borapentalene], C10H14BBrN2O2, does not modify significantly any structural parameter in the dioxazaborocane ring. On the other hand, a small asymmetry appears in the bond angles of the pyridine C atom next to the B atom.

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Section: Commentmentioning

confidence: 99%

2-(6-Bromopyridin-2-yl)-6-methyl-[1,3,6,2]dioxazaborocane, a new stable (pyridin-2-yl)boronic acid derivative

et al. 2004

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Synthesis and structures of new 1,3,6,2-dioxazaborocanes containing substituents in the ocane fragment

et al. 2008

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H, Ph) were synthesized by the reactions of aryl or methylboronic acids with dialkanolamines. The treatment of (Me 2 NCH 2 CH 2 O) 3 B (15) with MeN(CH 2 CH 2 OH)(CH 2 CPh 2 OH) afforded 2 [2 (dime thylamino)ethoxy] 1,3,6,2 dioxazaborocane (12). 2 Fluoro 1,3,6,2 dioxazaborocanes R 1 N(CHR 3 CHR 2 O)(CH 2 CH 2 O)BF (13: R 1 = PhCH 2 , R 2 = R 3 = H; 14: R 1 = Me, R 2 = R 3 = Ph, threo) were synthesized by the reaction of bis(trimethylsilyl) ethers of the corresponding di alkanolamines with BF 3 •Et 2 O. The new borocanes can be used for the synthesis of the corre sponding germanium derivatives PhCH 2 N(CH 2 CH 2 O) 2 GeX 2 (16, X = OEt; 17, X = Cl), as exemplified by the reaction of compound 6. The structures of erythro MeN(CH 2 CH 2 O)(CHPhCHPhO)BPh (3), threo MeN(CH 2 CH 2 O)(CHPhCHPhO)BPh (4), erythro MeN(CH 2 CH 2 O)(CHPhCHPhO)B(4 MeC 6 H 4 ) (8), and PhCH 2 N(CH 2 CH 2 O) 2 BF (13) were established by X ray diffraction. The coordination polyhedra of the boron atoms in these complexes can be described as distorted tetrahedra. The boron-nitrogen distances (1.705(7)-1.723(3) Å) provide unambiguous evidence for the presence of the B←N transannu lar interaction in these compounds. The structures of the resulting borocanes containing phenyl substituents at the carbon atoms of the ocane skeleton were studied by NMR spectroscopy and quantum chemical density functional theory calculations.

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Dioxazaborocanes: old adducts, new tricks

Bonin

Delacroix²,

Gras

2011

Org. Biomol. Chem.

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Dioxazaborocanes are boronic adducts obtained by condensation of diethanolamine derivatives with boronic compounds. They were first described in the mid-1950's as a practical way to isolate a boronic adduct. Their use has for a long time been restricted to this purpose for the isolation and characterisation of either a final product or a boronic intermediate. Only recently have they been directly involved in chemical transformations in which they proved equivalent or superior to their acid counterpart. In the meantime they have also been used as protected boronic acids. We wish to show in this report that they will likely represent a fluoride-free alternative to organotrifluoroborate salts and therefore an area of intense development.

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(E)-2-Styryl-[1,3,6,2]dioxazaborolane

Abstract: In the title compound, C12H16BNO2, the B—N distance is 1.662 (4) Å. Molecules are linked through intermolecular N—H⋯O hydrogen bonds to form infinite chains with an N⋯O distance of 2.810 (2) Å.

Cited by 3 publications

References 4 publications

2-(6-Bromopyridin-2-yl)-6-methyl-[1,3,6,2]dioxazaborocane, a new stable (pyridin-2-yl)boronic acid derivative

2-(6-Bromopyridin-2-yl)-6-methyl-[1,3,6,2]dioxazaborocane, a new stable (pyridin-2-yl)boronic acid derivative

Synthesis and structures of new 1,3,6,2-dioxazaborocanes containing substituents in the ocane fragment

Dioxazaborocanes: old adducts, new tricks

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