995. Chemistry related to borazole. Part II. The reaction of secondary amines with boron trichloride

Gerrard, W.; Hudson, H. R.; Mooney, E.F.

doi:10.1039/jr9600005168

Cited by 48 publications

(21 citation statements)

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“…Only the major component of the disordered structure is shown. The common distortion angles are α = 31.2(9), β/β′ = 36.00(13)/35.20(12), δ = 156.3(9), and θ = 103.38(15)°(for the definition of distortion angles and additional data see…”

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confidence: 99%

Insight into the Formation of Highly Strained [1]Ferrocenophanes with Boron in Bridging Position

et al. 2016

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Four planar-chiral, enantiomerically pure ferrocene dibromides (3 R1R2 ; [(CHR 1 R 2 )BrH 3 C 5 ] 2 Fe) equipped with two CHR 1 R 2 groups in α position to bromine were synthesized. From the four C 2 symmetrical species, two are already known [CHR 1 R 2 = CHMe 2 (3 MeMe ), CHEt 2 (3 EtEt )] and two are new compoundsThe dibromides 3 R1R2 were in situ converted into dilithio ferrocene derivatives and reacted with Cl 2 BNiPr 2 resulting in mixtures of bora[1]-ferrocenophanes (4 R1R2 ) and 1,1′-bis(boryl)ferrocenes (5 R1R2 ). The aim of this investigation was to test the hypothesis that the alkyl group that is oriented approximately perpendicular to the Cp ring, i.e., R 2 , affects the outcome of the salt-metathesis reaction. The obtained product ratios 4 R1R2 :5 R1R2 were determined by 1 H NMR spectroscopy and revealed that systems with the same R 2 group gave similar 4 R1R2 :5 R1R2 ratios (1.0:0.51 and 1.0:0.49 for R 2 = Me; 1.0:0.30 and 1.0:0.27 for R 2 = Et), confirming the hypothesis. Shown by DFT calculations (B3PW91/6-311+G(d,p)), reaction paths resulting in either product 4 R1R2 or product 5 R1R2 are both concerted steps.

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confidence: 99%

Insight into the Formation of Highly Strained [1]Ferrocenophanes with Boron in Bridging Position

et al. 2016

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“…Solvents were dried with a solvent purification system (SPS) from M. Braun columns and stored under argon over molecular sieves; reagents were dried and purified by standard procedures. Dibromo(diethylamino)borane, [29] dibromo(piperidino)borane, [30] Polymerization: A 500-mL glass autoclave equipped with a 15 mL dropping funnel was charged with toluene (200 mL) and methylaluminoxan solution (30 mL, 10 wt.-% in toluene). A solution of the complex (5 mL) in toluene (2·10 -3 ) was placed in the dropping funnel.…”

Section: Methodsmentioning

confidence: 99%

[1]Borahafnocenophanes: Synthesis, Structure and Catalytic Activity

et al. 2005

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“…After some seconds a suspension of the dilithiated product was formed. The reaction mixture was stirred for 1 h at room temperature, and then a solution of Cl 2 BNiPr 2 [13] (0.82 g, 4.5 mmol) in n-hexane (10 mL) was added drop by drop at room temperature. The reaction mixture was stirred at 508C for 3 h. Volatile material was pumped off, and the crude product was taken up in toluene (10 mL).…”

Section: Methodsmentioning

confidence: 99%

“…After the reaction mixture had been allowed to warm to room temperature, it was stirred for 1 h, then cooled to À 608C, and treated drop by drop with Cl 2 BNiPr 2 [13] (11.5 g, 63 mmol) in n-hexane (50 mL). The stirred mixture was allowed to warm to room temperature overnight, and the LiCl precipitate was removed by filtration through a glass frit (porosity 3 .…”

Section: Methodsmentioning

confidence: 99%