The Structure of the Organoboron Oxides

Kinney, Corliss R.; Pontz, Donald F.

doi:10.1021/ja01293a005

Cited by 25 publications

(23 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In 1936, Kinney and Pontz reported the first preparation of boroxines by heating the corresponding boric acids RB(OH) 2 (R = aryl) (Scheme 8, A). [24] Cyclic structure of boroxine was proposed based on its molecular weight. Considering the selective formation of the six-membered ring regardless of the nature of the organic substituents on the B atoms, the Snyder group hypothesized the presence of the resonance stabilization effect of the conjugated six π-electron system.…”

Section: Group 13/16mentioning

confidence: 99%

Inorganic Benzene Valence Isomers

Ota

Kinjo

2020

Chemistry An Asian Journal

View full text Add to dashboard Cite

It has been computationally proposed that there are more than 200 possible isomeric structures for the C6H6 molecule, among which benzene (CH)6 represents the most thermodynamically stable molecule and its chemistry has been extensively developed. Three benzene valence isomers (CR)6, namely, prismane, Dewar benzene, and benzvalene, have also been synthesized to date. Incorporation of heteroatoms in the skeletal frameworks allows access to inorganic analogues of benzene and its valence isomers, which have attracted considerable attention due to their peculiar structural and electronic features. Experimentally, more than 30 examples of inorganic benzene and its valence isomers have been developed and characterized so far. In this contribution, their synthesis and characterization, as well as their stability and chemical properties, are discussed.

show abstract

Section: Group 13/16mentioning

confidence: 99%

Inorganic Benzene Valence Isomers

Ota

Kinjo

2020

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…Examples include the long-known inorganic B 3 N n O O -baseds ix-membered rings displayed in Figure 1: borazine( B 3 N 3 ), [31] boroxadizine (B 3 N 2 O), [28][29][30] bordioxazine (B 3 NO 2 ) [28,29] and boroxine (B 3 O 3 ). [27] Amongst all inorganic rings, only the B 3 N 3 ,B 3 N 2 Oa nd B 3 NO 2 units can be completely integrated into fully planarized nanographene systems. One can hardly fail to notice that the B 3 N 3 ring can replace any benzenoid unit in am olecular graphene scaffold, whereas the B 3 N 2 Oa nd B 3 NO 2 rings can only be placed at the periphery.…”

Section: Introductionmentioning

confidence: 99%

Boron–Nitrogen‐Doped Nanographenes: A Synthetic Tale from Borazine Precursors

Dosso

Battisti

Ward

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

In this work, ac omprehensive account of the authors' synthetic efforts to prepareb orazino-doped hexabenzocoronenes by using the Friedel-Crafts-type electrophilic aromatic substitution is reported. Hexafluoro-functionalized aryl borazines, bearing an ortho fluoride leaving group on each of the N-and B-aryl rings,w as shown to lead to cascade-type electrophilica romatic substitution events in the stepwise CÀCbond formation, giving higher yields of borazinocoronenes than those obtained with borazine precursors bearing fluoride leavingg roups at the ortho positions of the B-aryl substituents. By using this pathway,a nu nprecedented boroxadizine-doped PAHf eaturing ag ulf-type periphery could be isolated,a nd itss tructure proven by single-crystal X-ray diffraction analysis. Mechanistic studies on the stepwise Friedel-Crafts-type cyclization suggestt hat the mechanism of the planarizationr eactionp roceeds through extension of the p system. To appraise the doping effect of the boroxadizine unit on the optoelectronic properties of topology-equivalent molecular graphenes, the all-carbon and pyrylium PAHa nalogues, all featuring ag ulf-type periphery, were also prepared. As already shown for the borazinodoped hexabenzocoronene, the replacement of the central benzene ring by its B 3 N 2 Oc ongener widens the HOMO-LUMO gap and dramaticallye nhances the fluorescence quantum yield.[a] J. Scheme1.Synthetic planarizationp rotocols for preparing borazino-doped hexabenzocoronenes 1 and 2.Figure 7. ESP surfaces mapped on the vdW surface up to an electrondensity of 0.05 electronbohr À3 for a) 11 and b) 18.Side (up) and top (bottom) view of the packingo fc )11 and d) 18.Atom colors:pink B, blue N, red O, gray C. Spacegroups: P2 1 /c and P1.

show abstract

“…Indeed, organoboron oxides, or oxoboranes, (RBO) have been known since the mid-1930s to exist as the anhydrides of boronic acids with cyclotrimeric structures assigned as (RBO) 3 , which are generally known as boroxines (1, Figure 1). [2] Significant effort has been focused on trying to generate the monomeric oxoboranes RBO, where multiple bonding between the boron atom and the oxygen atom would be required to stabilize these species. However, these elusive compounds have previously only been detected in the gas phase or by low-temperature matrix isolation studies.…”

mentioning

confidence: 99%

“…[5] The perfluoro aryl groups were crucial in preventing a competing insertion of the oxaborane oxygen atom into the CÀH bond of the adjacent R group. The adduct [HC (CMe) characterized by a number of analytical methods, including an X-ray diffraction study, which showed a BÀO bond length of 1.304 (2) . By comparison, the typical length of a BÀO bond found in boronic acids is about 1.36 .…”

mentioning

confidence: 99%

BO Chemistry Comes Full Circle

Westcott

2010

Angew Chem Int Ed

View full text Add to dashboard Cite

The Structure of the Organoboron Oxides

Cited by 25 publications

References 0 publications

Inorganic Benzene Valence Isomers

Inorganic Benzene Valence Isomers

Boron–Nitrogen‐Doped Nanographenes: A Synthetic Tale from Borazine Precursors

BO Chemistry Comes Full Circle

Contact Info

Product

Resources

About