A 1,3‐Diboratabenzene

Balzereit, Christian; Winkler, Heinz‐Jürgen; Massa, Werner; Berndt, A.

doi:10.1002/anie.199423061

Cited by 34 publications

(14 citation statements)

References 26 publications

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“…[9b] Its 11 B NMR spectrum shows a signal at δ ϭ Ϫ36 ppm, which might be due to the formation of the (σ-carboranyl)palladium iodide complex. Shore et al [10] have studied the reaction of Pd(PPh 3 ) 4 with the iodoborane clus-ter 9-I-1,7-(SMe 2 ) 2 B 12 H 9 and they observed similar results (δ 31 P ϭ 24.2/24.0 ppm).…”

Section: Regiospecific Substitution At the Basal Boron Atomsupporting

confidence: 77%

“…The mechanism of such Pdcatalyzed coupling reactions involving BϪI bonds [9a] is expected to be similar to that of carbonϪcarbon cross coupling, however the very first step in the catalytic cycle -the oxidative addition of the BϪI bond leading to a BϪPdϪI species -has not yet been verified. Stirring of a mixture of 2a and Pd(PPh 3 ) 4 in THF leads to a brown solution, whose 31 P NMR spectrum shows a signal at δ ϭ 22.4 ppm, which is in the expected region {[PdIPh(PPh 3 ) 2 ]: δ ϭ 22.3 ppm}. [9b] Its 11 B NMR spectrum shows a signal at δ ϭ Ϫ36 ppm, which might be due to the formation of the (σ-carboranyl)palladium iodide complex.…”

Section: Regiospecific Substitution At the Basal Boron Atommentioning

confidence: 99%

“…In the 1,6-dibromo case, substitution with the N-bonded (µ-NS)Fe 2 (CO) 6 cluster took place at the basal BϪBr bond, an excess of the nucleophile did not induce additional substitution at the 1-position. [3f] Berndt et al [4] have reported that the reduction of nido-(Me 3 SiC) 2 (CH) 2 (BtBu) 2 with Li in tetrahydrofuran affords a novel 1,3-diborabenzene anion, which could in turn be oxidized to give the starting carborane in refluxing 1,2-dibromoethane. As part of reactivity studies, we have reported transition metal derivatives of a benzo-C 4 B 2 nidocarborane compound [5a] with metal complex fragments coordinated to the benzene ring.…”

Section: Introductionmentioning

confidence: 99%

“…In both 9 and 10 two different types of clusters are directly connected by a B−C bond. Compound 1 reacts with ClZnC 6 H 4 C 6 H 4 ZnCl in the presence of the catalyst Pd(PPh 3 ) 4 to give 11, in which two C 4 B 2 clusters are linked by a C 6 H 4 C 6 H 4 unit. The constitutions of the products follow from spectroscopic data, and X-ray diffraction analyses for 2a, 2d, 4, 8, 9, and 10.…”

Section: Introductionmentioning

confidence: 99%

“…[3,4] To investigate substitution reactions in C 4 B 2 nido-carboranes, functional groups at the boron atom(s) other than alkyl groups are needed. Wrackmeyer et al were able to obtain 1,6-dibromo-2,3,4,5-tetracarba-nido-hexaboranes(6) [3a] by treating 1,4,6,9-tetraalkyl-3,8-diethyl-2,7-bis(diethylboryl)-5-stannaspiro [4.4]nona 3,6, .…”

Section: Introductionmentioning

confidence: 99%

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Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C₄B₂nido‐Carborane Derivatives

2004

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Keywords: Boron / Carboranes / Nucleophilic substitution / Iron / CobaltThe reactivity of the title compound 2,3,4,5-tetraethyl-1,6-diiodo-2,3,4,5-tetracarba-nido-hexaborane(6) (1) towards a variety of nucleophiles is reported. When 1 is treated with RC 2 Li (R = Ph, tBu, SiMe 3 , p-tolyl) and Ph 2 PLi, the corresponding new C 4 B 2 nido-carborane derivatives 2a−d and 3, respectively, are obtained by selective substitution at the basal B−I group, whereas the apical B−I bond remains inert. The reaction of 1 with K[(η 5 -C 5 H 5 )Fe(CO) 2 ] affords the novel species 4, which contains a CpFe(CO) 2 fragment σ-bonded to the basal boron atom of the C 4 B 2 cluster. Attempts to isolate 4 by chromatography on silica gel led to cleavage of the Fe−B bond and formation of compound 5, containing a basal BH vertex, which can be separately prepared by the reaction of 1 and LiBEt 3 H. In the reactions of 1 with PhLi and Me 3 SnLi, respectively, 6a and 7a are formed as the predominant B6-substituted carborane products. In addition, trace amounts of

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Section: Regiospecific Substitution At the Basal Boron Atomsupporting

confidence: 77%

Section: Regiospecific Substitution At the Basal Boron Atommentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C₄B₂nido‐Carborane Derivatives

2004

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Ein Fünfring mit drei negativen Ladungen und solvensfreien Lithium-Gegenionen

et al. 1999

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Aspects of the Chemical Energetics of Species with Carbon–Boron Bonds and Related Compounds

Slayden¹,

Liebman²

2020

Patai's Chemistry of Functional Groups

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In this chapter, we discuss selected energetics and thermochemical aspects of species with carbon–boron bonds. Although they lack a carbon–boron bond, atomic boron, its anion, and binary metal borides—the hypothetical alkali metal borides MB—and structurally complex metal borides are briefly introduced. Consideration of species with carbon–boron bonds begins with binary species such as the gas‐phase diatomic BC and the solid B 4 C and proceeds to the highly reactive methyl and phenyl derivatives of univalent borylene, BH. The question of regular behavior as homologous series is addressed for the relatively stable and long‐known classes of compounds, trialkylboranes and carboranes, with their normal (threefold) and higher boron‐coordination numbers. Trivalent boron and nitrogen species are then compared, first as organoboranes and amines, then as their organoborate and ammonium ions, and also as their “dimer” anions and cations. Pyridine borane complexes are likewise discussed and compared with benzene derivatives. Species with boron in the ring, borabenzenes and their amine complexes, are much more poorly understood. However, aromatic derivatives with both boron and nitrogen in the ring have evinced considerable interest, and the derivatives of the isomeric 1,2‐, 1,3‐, and 1,4‐azaborinines are described at some length. The chapter closes with species that contain oxygen along with boron, carbon, and hydrogen. Borane carbonyl (BH 3 CO), boronic acid derivatives, and boroxines are discussed.

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A 1,3‐Diboratabenzene

Cited by 34 publications

References 26 publications

Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C₄B₂nido‐Carborane Derivatives

Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C₄B₂nido‐Carborane Derivatives

Ein Fünfring mit drei negativen Ladungen und solvensfreien Lithium-Gegenionen

Aspects of the Chemical Energetics of Species with Carbon–Boron Bonds and Related Compounds

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A 1,3‐Diboratabenzene

Cited by 34 publications

References 26 publications

Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C4B2nido‐Carborane Derivatives

Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C4B2nido‐Carborane Derivatives

Ein Fünfring mit drei negativen Ladungen und solvensfreien Lithium-Gegenionen

Aspects of the Chemical Energetics of Species with Carbon–Boron Bonds and Related Compounds

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Product

Resources

About

Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C₄B₂nido‐Carborane Derivatives

Reactivity Studies on 2,3,4,5‐Tetraethyl‐1,6‐diiodo‐2,3,4,5‐tetracarba‐nido‐hexaborane(6): Synthesis and Structures of New C₄B₂nido‐Carborane Derivatives