7540-93-4

Upstream product

• 20736-40-7 2-(benzyloxy)-1,2-diphenylethanone 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 134-81-6 benzil 
• 6921-34-2 benzylmagnesium chloride 
• 451-40-1 phenyl benzyl ketone 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 1589-82-8 phenylmagnesium bromide 
• 4314-94-7 benzyl(trimethyl)tin 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 174869-02-4 α-(2-cyanoethyl)benzoin 
• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 

Downstream Products

• 4023-77-2 1-benzoyl-1,2-diphenylethylene 
• 26595-41-5 α-Benzyl-benzoin-ethylether 
• 56072-18-5 1,2,3-triphenyl-propane-1,2-diol 
• 27962-37-4 α-Benzyl-benzoin-methylether 
• 451-40-1 phenyl benzyl ketone 
• 100-52-7 benzaldehyde 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 4842-45-9 1,2,3-triphenylpropan-1-one 
• 5773-56-8 1,2-Diphenylethanol 
• 65-85-0 benzoic acid 
• 91-01-0 1,1-Diphenylmethanol 
• 5343-98-6 4-oxo-4-phenylbutanenitrile 
• 95448-28-5 α-(4-methylbenzyl)benzoin 
• 174869-02-4 α-(2-cyanoethyl)benzoin 

Relevant academic research and scientific papers

Photo-allylation and photo-benzylation of carbonyl compounds using organotrifluoroborate reagents

Allyl- and benzyl-trifluoroborates can be applied to the photoreaction of carbonyl compounds to afford the corresponding alcoholic adducts in acceptable yields via a photo-induced single electron transfer pathway. The results were confirmed from the react

First examples of hypervalent enhancement of photoallylation by allylsilicon compounds via photoinduced electron transfer

Hypervalency (pentacoordination) of silicon atom enhanced photoallylation of 1,2-diketones with allylsilicon reagents, while normal tetracoordinated ones could not. This reaction seems to proceed via photoinduced electron transfer from the silicon reagent

Carbon-carbon bond cleavage of α-substituted benzoins by retro-benzoin condensation; A new method of synthesizing ketones

When α-benzylbenzoin (3a, α-benzyl-α-hydroxybenzyl phenyl ketone) was treated with potassium cyanide (1) in N,N-dimethylformamide at 80°C for 1h, the carbon-carbon bond was cleaved, resulting in the formation of deoxybenzoin (4a, benzyl phenyl ketone) and benzaldehyde (2a). This carbon- carbon bond cleavage proceeds through a retro-benzoin condensation mechanism. This method of synthesizing ketones was applied to several α-substituted benzoins (3), and the corresponding ketones (4) were formed in good yields. Further, we found that the cyanide ion-donating ability of tetrabutylammonium cyanide (6, Bu4NCN) is more effective than that of potassium cyanide (1, KCN). As expected from the chemical analogy between cyanide ion and azolium ylide, several azolium salts (7) can also be employed in the retro-benzoin condensation as catalysts. The benzoin derivatives 3 were synthesized in the following three ways; reaction of alkyl halide (9) with benzoin (5), Michael addition of benzoin (5) with acceptors (10), and Grignard reaction of benzils (8). Alkylation of the benzoins without isolation, followed by carbon-carbon bond cleavage, readily afforded the corresponding ketones (4).

Allylation of α-Diketones by Photochemical Reactions with Allylic Stannanes. Regiochemistry of Introduced Allylic Group

Irradiation of an acetonitrile solution of benzils and acenaphthenequinone in the presence of allylic stannanes afforded homoallylic alcohols in good yields.In the reaction with unsymmetric allylstannanes, the allylic groups were introduced predominantly at α-positions.The completely regioselective introduction could be achieved by the irradiation in the presence of NaOH or CoCl2 as an additive.

The Reaction of Benzil with Grignard Reagents

Benzil reacts with Grignard reagents forming, in the first step, the 1,2-addition product (C-alkylation), but often also the 1,4-addition product (O-alkylation) and the reduction product, benzoin.The product distribution has been determined for mechanistic purposes for 16 Grignard reagents using a standard procedure.These results, and observations made using deuteriated reagents and the 5-hexenyl radical probe indicate an electron transfer (ET) mechanism for reagents having hydrogen in the β-position, while a polar mechanism is the most efficient for methyl, phenyl, benzyl and allyl Grignard reagents in the ether solution.For the ET mechanism, a six-centre transition state is suggested.Furthermore, a distinction is made between the primary cage product (O-alkyl) resulting from immediate combination of the radical pair, and the secondary cage product (C-alkyl) formed in the cage after rearrangement. 5-Hexenylmagnesium bromide yields uncyclised primary and secondary cage product, but also significant amounts of cyclised C-alkylation product formed by escape of the radicals from the cage and re-encounter after cyclisation of 5-hexenyl to cyclopentylmethyl.A recently suggested mechanism based on the existence of stable radical ion pairs is found to be unacceptable.