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

Meller, A.; Bromm, D.; Maringgele, W.; Böhler, Dieter; Elter, G.

doi:10.1016/0022-328x(88)80264-x

Cited by 27 publications

(5 citation statements)

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“…An early work demonstrating the ring-opening of benzene by a main-group compound was reported by Meller in 1988 on the reduction of a dihaloaminoborane in a benzene/dimethoxyethane solvent mixture, which led to the formation of a diboron derivative of pentalene. 21 In 2019, the groups of Goicoechea and Aldridge presented the reversible insertion of a reactive aluminium anion into benzene at 80 °C, the product of which was trapped using Me 2 SnCl 2 . 22 In our case, to confirm that the solvent was the source of the backbone of the product 4 , we repeated the reaction in toluene at room temperature.…”

Section: Resultsmentioning

confidence: 99%

Generation of a transient base-stabilised arylalumylene for the facile deconstruction of aromatic molecules

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Generation of a transient base-stabilised arylalumylene for the facile deconstruction of aromatic molecules

et al. 2022

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“…Aminoborylene 3a (R = H) was detected by Thompson et al . in an argon matrix after co-deposition of laser ablated boron atoms with ammonia, while Meller and co-workers have successfully trapped derivatives of 3 . − The barrier to [1,2]-H migration in 3a , 27 kcal mol -1 from theory, is significantly larger than that in 1a . Both 1a and 3a have singlet ground states; the triplet state of 1a lies significantly higher in energy …”

Section: Introductionmentioning

confidence: 99%

Donor Stabilized Borylnitrene: A Highly Reactive BN Analogue of Vinylidene

Bettinger

Bornemann

2006

J. Am. Chem. Soc.

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A donor atom stabilized borylnitrene, 2-nitreno-1,3,2-benzodioxaborole 4c, is characterized by matrix isolation IR, UV, and ESR spectroscopy as well as multiconfiguration SCF and CI computations. UV irradiation (λ ) 254 nm) of the corresponding azide 6c, isolated in solid argon at 10 K, produces 4c in high yield. The oxygen donor atoms in 4c result in a triplet ground state (|D/hc| ) 1.492 cm -1 , |E/hc| ) 0.004 cm -1 ) for the borylnitrene. The lowest energy singlet state ( 1 A1) is 33 kcal mol -1 higher in energy and closely related to the ground state of vinylidene. Under the conditions of matrix isolation, triplet 4c is photochemically and thermally stable toward rearrangement to the corresponding cyclic iminoborane. Photochemical irradiation (λ > 550 nm) of 4c rather causes an efficient reaction with molecular nitrogen, lying in matrix sites nearby, to give 6c. Similarly, photochemical, but not thermal, trapping of 4c with CO is possible and results in the corresponding isocycanate 9c. Thermal reaction of 4c with O 2 in doped argon matrixes at 35 K could be observed by IR spectroscopy to result in borylnitroso-O-oxide 17c as shown by 18 O2 labeling experiments and DFT computations. The diradical 17c is very photolabile and quickly rearranges to the nitritoborane 16c upon irradiation.

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“…Probably the formation of the five-membered ring in this case favors the 1,2-addition. It should be noted that 1,4-additions of boron species to naphthalene , by one or two boron atoms are well documented. Likewise, naphthalene species that are diborylated in the 1,8-positions are obtained from the 1,8-dilithiated − or the 1,8-dimercurated , precursors.…”

Section: Resultsmentioning

confidence: 99%

Bis(diorganylamino)dihalodiboroxanes as Building Blocks for Boron Heterocycles

1997

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Bis(diorganylamino)dihalo-1,3-diboroxanes 1 result from the controlled hydrolysis of (diorganylamino)dihaloboranes substituted with bulky dialkyl- or alkylarylamino groups. Dehalogenation with sodium/potassium alloy gives 1,4-dioxa-2,3,5,6-tetraborinanes 3 and, in the case of the di(s-butyl)amino groups, the corresponding oxadiborirane 4. If the dehalogenation is carried out in the presence of bi- or tricyclic aromatic compounds, addition of a B(NR2)OB(NR2) moiety is observed, and the corresponding 1,3-(1,2-dihydronaphthaline-1,2-diyl)diboroxane (5), 1,3-(9,10-dihydroanthracene-9,10-diyl)diboroxane (6), and 1,3-(9,10-dihydrophenanthrene-9,10-diyl)diboroxane (7) species are obtained. The compounds were characterized by NMR spectroscopy (1H, 11B, 13C), MS (EI and FI), and elemental analyses. X-ray crystal structure determinations are presented for 1a, 3a, 5a, and 6b.

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

Cited by 27 publications

References 5 publications

Generation of a transient base-stabilised arylalumylene for the facile deconstruction of aromatic molecules

Generation of a transient base-stabilised arylalumylene for the facile deconstruction of aromatic molecules

Donor Stabilized Borylnitrene: A Highly Reactive BN Analogue of Vinylidene

Bis(diorganylamino)dihalodiboroxanes as Building Blocks for Boron Heterocycles

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