33713-72-3

Upstream product

• 122-78-1 phenylacetaldehyde 
• 96-09-3 styrene oxide 
• 101-97-3 Ethyl 2-phenylethanoate 

Downstream Products

• 122-78-1 phenylacetaldehyde 

Relevant academic research and scientific papers

Manganese and rhenium-catalyzed selective reduction of esters to aldehydes with hydrosilanes

The selective reduction of esters to aldehydes, via the formation of stable alkyl silyl acetals, was, for the first time, achieved with both manganese, -Mn2(CO)10- and rhenium -Re2(CO)10- catalysts in the presence of triethylsilane as reductant. These two methods provide a direct access to a large variety of aliphatic and aromatic alkyl silyl acetals (30 examples) and to the corresponding aldehydes (13 examples) upon hydrolysis. The reactions proceeded in excellent yields and high selectivity at room temperature under photo-irradiation conditions (LED, 365 nm, 40 W, 9 h).

Synthesis of 1,3,5-trioxanes: Catalytic cyclotrimerization of aldehydes

A series of 1,3,5-trioxanes derived from a single aldehyde, or from two aldehydes, were synthesized with methylrhenium trioxide as a catalyst. Cyclotrimerization of the aldehydes gave excellent yields under proper conditions, as did diethyl ketomalonate. A possible intermediate in the case of propionaldehyde was observed using 1H NMR spectroscopy. Water inhibits both forward and reverse reactions.

Breaking C-O Bonds with Uranium: Uranyl Complexes as Selective Catalysts in the Hydrosilylation of Aldehydes

We report herein the possibility to perform the hydrosilylation of carbonyls using actinide complexes as catalysts. While complexes of the uranyl ion [UO2]2+ have been poorly considered in catalysis, we show the potentialities of the Lewis acid [UO2(OTf)2] (1) in the catalytic hydrosilylation of a series of aldehydes. [UO2(OTf)2] proved to be a very active catalyst affording distinct reduction products depending on the nature of the reductant. With Et3SiH, a number of aliphatic and aromatic aldehydes are reduced into symmetric ethers, while iPr3SiH yielded silylated alcohols. Studies of the reaction mechanism led to the isolation of aldehyde/uranyl complexes, [UO2(OTf)2(4-Me2N-PhCHO)3], [UO2(μ-κ2-OTf)2(PhCHO)]n, and [UO2(μ-κ2-OTf)(κ1-OTf)(PhCHO)2]2, which have been fully characterized by NMR, IR, and single-crystal X-ray diffraction.

Performance and coke species of HZSM-5 in the isomerization of styrene oxide to phenylacetaldehyde

The performance and coke species of HZSM-5 in the isomerization of styrene oxide to phenylacetaldehyde was investigated under gas phase, free of solvents. The reaction showed higher catalytic stability and phenylacetaldehyde selectivity at around 300 °C, lower feed rate (e.g., WHSV = 1.2-3 h-1) and higher flow rate of carrier gas (e.g., 120 mL min-1). Based on FT-IR spectra, the dimer formed via aldol condensation of phenylacetaldehyde was one of the precursors of coke species. TG results showed that there were two types of coke species. The soft coke, which can be removed via desorption between 200-400 °C, had less influence on the catalytic stability. The hard coke, which had a certain degree of crystallization (i.e., pregraphite-like carbon presenting in XRD patterns) and must be completely removed via burning with oxygen, causes major catalyst deactivation.

Antimony(v) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes

1-Diphenylphosphinonaphthyl-8-triphenylstibonium triflate ([2][OTf]) was prepared in excellent yield by treating 1-lithio-8-diphenylphosphinonaphthalene with dibromotriphenylstiborane followed by halide abstraction with AgOTf. This antimony(v) cation was found to be stable toward oxygen and water, and exhibited exceptional Lewis acidity. The Lewis acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf] catalyzed the cyclotrimerization of aliphatic and aromatic aldehydes to afford the industrially-useful 1,3,5 trioxanes (N) in good yields, and with great selectivity. This phosphine-stibonium motif represents one of the first catalytic systems of its kind that is able to catalyze these reactions with aldehydes in a controlled, efficient manner. The mechanism of these processes has been explored both experimentally and theoretically. In all cases the Lewis acidic nature of the antimony(v) cation was found to promote these reactions.

Synthesis and reactions of N,N-bis[1-(trimethylsiloxy)alkyl]-formamides: Preparation of (±)-argemonine and (±)-norargemonine

Symmetrical and unsymmetrical N,N-bis[1-(trimethylsiloxy)alkyl]formamides are prepared and their reactions investigated, including an application to the synthesis of the pavine alkaloids (±)-argemonine and (±)-norargemonine.

Reactions of Phenylacetaldehydes in Fluorosulfuric Acid

The treatment of phenylacetaldehydes in fluorosulfuric acid generates 2,3,6,7-dibenzo-9-oxabicyclonona-2,6-dienes.The generality of this reaction was tested on several derivatives which were substituted either at the 2-position or on the ring.Diastereoisomers, whenever obtained, were characterized by a combination of X-ray analysis and NMR data.Phenylacetone reacted differently and afforded the products of electrophilic aromatic substitution by fluorosulfuric acid.The structure of the unexpected minor reaction products was elucidated.