Organic Compounds Of Boron

Läppert, Michael F.

doi:10.1021/cr50011a002

Cited by 205 publications

(92 citation statements)

References 202 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…It was found that triphenylboron can be easily contaminated through various stages of hydrolysis that give phenylboronic anhydride (C,H,BO),, phenylboroi~ic acid C,H,B(OH),, and diphenyl phenylboronate C,H,B(OC,H,), (2,3). Therefore, in conjunction with our spectral study of triphenylboron (I), a detailed spectroscopic investigation on these contaminants seemed worthwhile.…”

Section: Introductionmentioning

confidence: 90%

“…Because diphenyl phenylboronate is easily hydrolyzed, its preparation was carried out in an inert atmosphere of dry nitrogen. The compound was prepared by the esterification of phenylboron dichloride with phenol (3,17,18) under dry nitrogen. The absence of any absorption band between 3300-3200 crn-due to an 0-H stretching vibration or near 1000 cm-' due to a B-0-H deformation mode in the spectrum indicated the absence of 0-H bonds and was thus a proof of the purity of the sample.…”

Section: Symmetry Considerationmentioning

confidence: 99%

See 1 more Smart Citation

Infrared spectra of phenylboronic acid (normal and deuterated) and diphenyl phenylboronate

Faniran¹,

Shurvell²

1968

Can. J. Chem.

137

View full text Add to dashboard Cite

The infrared spectra of phenylboronic acid, normal and deuterated, and diphenyl phenylboronate have been recorded in the range 4000-300 cm-' and assignments of the observed frequencies have been made. The spectrum of the acid in the OH stretching region shows evidence of intramolecular hydrogen bonding. The spectrum of diphenyl phenylboronate has been interpreted by analogy with monosubstituted benzene derivatives. The two different environments of the phenyl groups in this molecule give rise to splitting of two of the characteristic vibrations of the benzene ring near 760 and 680 cm-I.

show abstract

Section: Introductionmentioning

confidence: 90%

Section: Symmetry Considerationmentioning

confidence: 99%

Infrared spectra of phenylboronic acid (normal and deuterated) and diphenyl phenylboronate

Faniran¹,

Shurvell²

1968

Can. J. Chem.

137

View full text Add to dashboard Cite

show abstract

“…This may also explain why > 1 equivalent of the aryl boronic acid results in enhanced yields. [135] Moreover, the aryl boronic acid can form triaryl boroxines [136] and in doing so forms water, which can be removed from the reaction by molecular sieves. Evans and coworkers postulated that phenolic products are formed as a result of the competitive arylation of water formed during the reaction process.…”

Section: Angewandte Chemiementioning

confidence: 99%

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

Ley,

Thomas

2003

Angew Chem Int Ed

2,517

816

View full text Add to dashboard Cite

The copper-mediated C(aryl)[bond]N, C(aryl)[bond]O, and C(aryl)[bond]S bond formation is an important transformation and has been developed to include a wide range of substrates. This Review highlights the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids, aryl halides, iodonium salts, siloxanes, stannanes, plumbanes, bismuthates, and trifluoroborate salts as aryl donors. In particular, the recent introduction of boronic acids as reaction partners in both O- and N-arylation has been a significant discovery and will occupy centre-stage in this review. Clear improvements can be obtained by the correct choice of copper source, base, ligands, and other additives. Mechanistic investigations should provide insight into the catalytically active species, which would aid in the development of milder, more-efficient methods.

show abstract

“…An allplanar D,, structure is unlikely, because the overlap of the Van der Waals' spheres of the ortho hydrogen atoms would be expected to give rise to twisting of the phenyl groups out of the plane of the BC, group, so that a propellershaped molecule with symmetry D, would result. We assume that triphenylborate like the alkylborates exists as a monomer (18) and that the BO, skeleton is planar (19,20). Examination of molecular models of triphenylborate shows that the most symmetrical configuration is the one in which all the benzene rings are coplanar with the BO, plane.…”

Section: Symmetry and Structurementioning

confidence: 99%

Infrared spectra of triphenylboron and triphenylborate

Shurvell¹,

Faniran²

1968

Can. J. Chem.

View full text Add to dashboard Cite

The infrared spectra of triphenylboron and triphenylborate have been obtained in the region 4000 to 300cm-'. The analysis of the spectra supports a propeller-shaped structure with symmetry D3 for triphenylboron and a planar structure with symmetry C j h for triphenylborate. The Urey-Bradley force field has been applied to the calculation of approxin~ate vibrational force constants for the BC3 and B 0 3 groups.Les spectres infrarouges du triphtnylbor et triphenylborate ont kt6 enregistres entre 4000 et 300 cm-I. L'analyse des spectres indique une structure helice avec symetrie D3 pour triphenylbor et une structure plane avec symktrie C3,, pour triphenylborate. Le champs de force Urey-Bradley a ett utilise pour calculer des constantes de force pour Ics groilpes BC3 et BO,.

show abstract

Organic Compounds Of Boron

Cited by 205 publications

References 202 publications

Infrared spectra of phenylboronic acid (normal and deuterated) and diphenyl phenylboronate

Infrared spectra of phenylboronic acid (normal and deuterated) and diphenyl phenylboronate

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

Infrared spectra of triphenylboron and triphenylborate

Contact Info

Product

Resources

About