A tricyclic ring system of six carbon and five boron atoms from monoalkylbenzene and five formal borene units

Maringgele, W.; Seebold, U.; Heine, A.; Noltemeyer, Mathias; Sheldrick, George M.; Meller, A.

doi:10.1021/om00053a006

Cited by 9 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A tricyclic ring/cage system of RC 6 H 5 ·5BNR' 2 products were formed by reactions between dehalogenation products of F 2 BN( i -Pr) 2 with monoalkylbenzenes using monoglyme as the co-solvent. 274 Hung et al 275 prepared linear and cyclic perfluorinated polyethers through the ionic polymerization of a trifluorovinyl ether alcohol (CF 2 =CFOR f CH 2 OH, R f = CF 2 CF(CF 3 )OCF 2 CF 2 ) and the subsequent fluorination of the polyfluorinated polyethers (Scheme 32). They found that without a solvent, linear polymers with M n values up to 29,000 were produced, while in glyme solution, cyclic oligomers were major products and a cyclic dimer was obtained in yields up to 60%.…”

Section: Uses In Organic Reactionsmentioning

confidence: 99%

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

2014

View full text Add to dashboard Cite

Glymes, also known as glycol diethers, are saturated non-cyclic polyethers containing no other functional groups. Most glymes are usually less volatile and less toxic than common laboratory organic solvents; in this context, they are more environmentally benign solvents. However, it is also important to point out that some glymes could cause long-term reproductive and developmental damages despite their low acute toxicities. Glymes have both hydrophilic and hydrophobic characters that common organic solvents are lack of. In addition, they are usually thermally and chemically stable, and can even form complexes with ions. Therefore, glymes are found in a broad range of laboratory applications including organic synthesis, electrochemistry, biocatalysis, materials, and Chemical Vapor Deposition (CVD), etc. In addition, glyme are used in numerous industrial applications, such as cleaning products, inks, adhesives and coatings, batteries and electronics, absorption refrigeration and heat pumps, as well as pharmaceutical formulations, etc. However, there is a lack of comprehensive and critical review on this attractive subject. This review aims to accomplish this task by providing an in-depth understanding of glymes’ physicochemical properties, toxicity and major applications.

show abstract

Section: Uses In Organic Reactionsmentioning

confidence: 99%

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

2014

View full text Add to dashboard Cite

show abstract

“…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.

View full text Add to dashboard Cite

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.

show abstract

Triaminotriborane(3): A Homocatenated Boron Chain Connected by B−B Multiple Bonds

et al. 2017

View full text Add to dashboard Cite

A triaminotriborane(3) was isolated as purple crystals through the reduction of (TMP)BCl2 (TMP=2,2,6,6‐tetramethylpiperidino) by sodium naphthalenide. Single‐crystal X‐ray diffraction and computational studies of the obtained triaminotriborane(3) revealed a bent structure of the [B(NR2)]3 chain. The bond lengths between the central and terminal boron atoms were similar to those observed in neutral diborene species. The multiple‐bonding character may be best described by a three‐center two‐electron π‐bond along the B3 chain. The distance between the two terminal boron atoms (2.177 Å) in the solid‐state structure implies a weak interaction between them. When an excess amount of Li was used as the reducing agent, the reaction yielded an unusual dianionic species. The isolation and characterization of these two reduction products are reported herein.

show abstract

A tricyclic ring system of six carbon and five boron atoms from monoalkylbenzene and five formal borene units

Cited by 9 publications

References 0 publications

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

Donor Stabilized Borylnitrene: A Highly Reactive BN Analogue of Vinylidene

Triaminotriborane(3): A Homocatenated Boron Chain Connected by B−B Multiple Bonds

Contact Info

Product

Resources

About