1694-84-4

Basic information

• Product Name: Borane, tris(phenylmethyl)-
• CAS NO: 1694-84-4
• Molecular Formula: C21H21B
• Molecular Weight: 284.209
• Mol File: 1694-84-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Borane, tris(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Borane, tris(phenylmethyl)-(1694-84-4)
• EPA Substance Registry System: Borane, tris(phenylmethyl)-(1694-84-4)

Safety Data

• Hazardous Substances Data: 1694-84-4(Hazardous Substances Data)

Upstream product

• 6921-34-2 benzylmagnesium chloride 
• 620-05-3 iodomethylbenzene 
• 16510-43-3 benzylidenetriphenylphosphorane-borane 
• 365215-43-6 (N,N'-diisopropylaminotroponiminate)Al(CH₂Ph)2 
• 199607-72-2 (Me₂Si(NCMe₃)2)Zr(benzyl)(benzyl-B(pentafluorophenyl)3) 
• 109-63-7 boron trifluoride diethyl etherate 
• 100-39-0 benzyl bromide 

Downstream Products

• 40654-82-8 4-phenyl-2-methylbutanal 
• 60218-11-3 Diaethyl-(benzyl)-boran 
• 2179-97-7 2-(1,1-dibenzyl-2-phenyl-ethyl)-1,3-diphenyl-[1,3,2]diazaborolidine 
• 25870-62-6 1-phenyl-2-hexanone 
• 22086-65-3 (benzyl)difluoroborane 
• 22072-81-7 (dibenzyl)chloroborane 
• 23065-87-4 Lithium-tetrabenzylborat 
• 22413-90-7 sodium tetrabenzylborate 
• 34491-91-3 4-Benzyl-4-hydroxy-1(4H)naphthalinon 
• 16396-49-9 N-benzyl-N'-(ethoxycarbonyl)ethoxycarbohydrazide 
• 97-94-9 triethyl borane 
• 69464-75-1 (benzyl)dibromoborane 
• 127668-05-7 (C₆H₅CH₂)3B(CO) 
• 2467-18-7 boric acid tribenzyl ester 

Relevant articles and documents

Indium-Mediated Synthesis of Benzylic Hydroperoxides

An indium(0)-metal-mediated efficient synthesis of benzylic hydroperoxides is described. The reaction proceeds efficiently with a broad range of benzyl bromides under aerobic conditions at room temperature to afford benzyl hydroperoxides in good to excellent yields. In addition, the tandem hydroperoxidation-Michael addition of (E)-1-(bromomethyl)-2-(2-nitrovinyl)benzene was also demonstrated.

C-N bond formation on addition of aryl carbanions to the electrophilic nitrido ligand in TpOs(N)Cl2

The osmium (VI) nitrido complex TpOs(N)Cl2 (1) has been prepared from K[Os(N)O3] and KTp in aqueous ethanolic HCl. It reacts rapidly with PhMgCl and related reagents with transfer of a phenyl group to the nitrido ligand. This forms Os(IV) metalla-analido complexes, which are readily protonated to give the analido complex TpOs(NHPh)Cl2 (4). The nitrido-phenyl derivatives TpOs(N)PhCl and TpOs(N)Ph2 react more slowly with PhMgCl and are not competent intermediates for the reaction of 1 with PhMgCl. Reactions of 1 with alkyl- and arylboranes similarly result in transfer of one organic group to nitrogen, leading to isolable borylamido complexes such as TpOs[N(Ph)(BPh2)]Cl2 (11). This is an unprecedented insertion of a nitrido ligand into a boron - carbon bond. Hydrolysis of 11 gives 4. Mechanistic studies suggest that both the Grignard and borane reactions proceed by initial weak coordination of Mg or B to the nitrido ligand, followed by migration of the carbanion to nitrogen. The hydrocarbyl group does not go to osmium and then move to nitrogen - there is no change in the atoms bound to the osmium during the reactions. It is suggested that there may be a general preference for nucleophiles to add directly to the metal - ligand multiple bond rather than binding to the metal first and migrating. Ab initio calculations show that the unusual reactivity of 1 results from its accessible LUMO and LUMO + 1, which are the Os≡N π* orbitals. The bonding in 1 and its reactivity with organoboranes are reminiscent of CO.

Monoalkylborane aus Alkyliden(triphenyl)phosphoranen und Boran; Kombination von Ylidreaktionen und Hydroborierung

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