Synthesis and characterization of new azido(o-phenylenedioxy)boranes and azidobicyclononylboranes †

Fraenk, Wolfgang; Habereder, Tassilo; Klapötke, Thomas M.; Nöth, Heinrich; Polborn, Kurt

doi:10.1039/a907222e

Cited by 20 publications

(25 citation statements)

References 17 publications

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“…The dimensions of the 9-borabicyclo[3.3.1]nonane group are comparable to those found in related structures (Brock et al, 1992;Fraenk et al, 1999;Yalpani et al, 1990;Wrackmeyer et al, 1995). The B-C bond lengths are 1.6150 16…”

Section: Figuresupporting

confidence: 82%

(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C¹,C⁵)boronium trifluoromethanesulfonate

Ma¹,

Bats²

2001

Acta Cryst E

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Section: Figuresupporting

confidence: 82%

(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C¹,C⁵)boronium trifluoromethanesulfonate

Ma¹,

Bats²

2001

Acta Cryst E

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“…The IR spectrum of 1 features a strong band at 2112 cm −1 , also consistent with the presence of an azide group covalently attached to boron (the ν asym N 3 band in covalently bound azides is usually observed at ca. 2100 cm −1 ) and in good agreement with predicted frequencies (see Supporting Information). 1 is also formed when an azide salt, [PPh 4 ]N 3 , is used as the azide source.…”

Section: Figurementioning

confidence: 99%

Diborane(4) Azides: Surprisingly Stable Sources of Transient Iminoboranes

et al. 2020

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Herein we describe the first examples of isolable electron‐precise diboranes(4) that bear azide moieties: the acyclic 1,2‐diazido‐1,2‐bis(dimethylamino)diborane(4) and the cyclic 1,4‐diaryl‐2,3‐diazido‐1,4‐diaza‐2,3‐diborinines (aryl=mesityl, 2,6‐xylyl, 4‐tolyl). The reported examples are not only stable enough to be observed and isolated (putative transient diborane(4) azides previously reported by our group spontaneously decompose even below room temperature), but some of them are even robust enough to undergo controlled pyrolysis without explosive decomposition at temperatures well above 100 °C. In two cases, the controlled pyrolysis allows the isolation of complex diazaboretidines, which are the apparent dimerization products of endocyclic boryl‐iminoboranes.

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“…CatBN 3 was synthesized according to ap ublished procedure. [22] Matrix-isolation experiments were performed by standard techniques on aS umitomo SH-1 closed-cycle helium cryostat. [23] Matrices were produced by deposition of different materials, such as argon, nitrogen, and neon (Messer-Griesheim, 99.9999 %), on top of aC sI (IR) window at 15, 10, and 4K,r espectively,w ith oxygen as a dopant (2-3 %, 99.999 %p urity).…”

Section: Experimental Section Experimentsmentioning

confidence: 99%

Unusual Nitrene Oxidation Product Formation by Metathesis Involving the Dioxygen O−O and Borylnitrene B−N Bonds

Bhagat

Schumann

Bettinger

2020

Chemistry A European J

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The reactiono fd ioxygen with nitrenes can have significant energy barriers, although both reactants are triplet diradicals and the formationof nitroso-O-oxides is spin-allowed.B ym eans of matrix-isolation infrared spectroscopy in solid argon, nitrogen, and neon,a nd through high-level computational quantum chemistry,i ti ss hownh erein that a 3-nitreno-1,3,2-benzodioxaborole CatBN (Cat = catecholato) reacts with dioxygenu nder cryogenicc onditions thermally at temperatures as low as 7K to produce two distinct products, an anti-nitroso-O-oxide and an itritoborane CatBONO. The computedb arriers for the formation of nitroso-O-oxide isomersa re very low.W hereas anti-nitroso-O-oxide is kinetically trapped,i ts bisected isomer has av ery low barrierf or metathesis, yieldingt he CatBO + NO radicals in as trongly exothermic reaction; these radicals can combineu nder matrix-isolation conditions to give nitritoborane CatBONO. The trapped isomer, anti-nitroso-O-oxide, can form the nitri-toboraneC atBONO only after photoexcitation, possibly involvingi somerization to the bisectedi somer of anti-nitroso-O-oxide.

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Synthesis and characterization of new azido(o-phenylenedioxy)boranes and azidobicyclononylboranes †

Cited by 20 publications

References 17 publications

(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C¹,C⁵)boronium trifluoromethanesulfonate

(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C¹,C⁵)boronium trifluoromethanesulfonate

Diborane(4) Azides: Surprisingly Stable Sources of Transient Iminoboranes

Unusual Nitrene Oxidation Product Formation by Metathesis Involving the Dioxygen O−O and Borylnitrene B−N Bonds

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Synthesis and characterization of new azido(o-phenylenedioxy)boranes and azidobicyclononylboranes †

Cited by 20 publications

References 17 publications

(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C1,C5)boronium trifluoromethanesulfonate

(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C1,C5)boronium trifluoromethanesulfonate

Diborane(4) Azides: Surprisingly Stable Sources of Transient Iminoboranes

Unusual Nitrene Oxidation Product Formation by Metathesis Involving the Dioxygen O−O and Borylnitrene B−N Bonds

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(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C¹,C⁵)boronium trifluoromethanesulfonate

(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C¹,C⁵)boronium trifluoromethanesulfonate