10568-31-7

Upstream product

• 103-26-4 Methyl cinnamate 
• 4192-77-2 ethyl cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 102-92-1 Cinnamoyl chloride 

Downstream Products

• 77249-46-8 (E)-cinnamaldehyde-α-d₁ 
• 75376-94-2 <αα-2H2>cinnamyl bromide 
• 464169-84-4 2-trimethylsilyldideuteriomethyl-3-phenyl-oxirane 
• 77249-47-9 trans 1-phenyl<3-(2)H>buta-1,3-diene 
• 1620657-45-5 2,2-bisdeuterio-3,3-diphenylpropanol 
• 1620657-23-9 diethyl (E)-1,1-bis(deuterio)-3-phenyl-2-propenylphosphate 
• 50742-91-1 N-(<αα-2H2>cinnamyl)-2-hydroxy-NN-di(<2H3>methyl)anilinium bromide 
• 79833-35-5 N-(<αα-2H2>cinnamyl)-NN-di(<2H3>methyl)anilinium-2-olate 
• 103-65-1 phenylpropane 

Relevant academic research and scientific papers

Catalytic aerobic oxidation of allylic alcohols to carbonyl compounds under mild conditions

A new catalytic aerobic oxidation of alcohols to aldehydes under green conditions was developed (room temperature and pressure, water solution, open vials). The water-soluble platinum(II) tetrasulfophthalocyanine (PtPcS) catalyst showed the best selectivity for carbonyl derivatives, and in particular for α,β-unsaturated alcohols; the reactions are slow.

Rhodium-Catalyzed Synthesis of α,β-Unsaturated Ketones through Sequential C-C Coupling and Redox Isomerization

A novel Rh(I)-catalyzed sequential C-C coupling and redox isomerization between allylic alcohols and 1,3-dienes has been accomplished. This versatile protocol provides expeditious access to a broad range of polysubstituted α,β-unsaturated ketones with excellent atom economy and regioselectivity.

Silylative cyclopropanation of allyl phosphates with silylboronates

A potassium-bis(trimethylsilyl)amide-mediated cyclopropanation of allyl phosphates with silylboronates has been developed. Unlike the reported copper-catalyzed allylic substitution reactions, the nucleophile selectively attacks at the β-position of the allylic substrates under the present reaction conditions. The mechanism of this process has also been investigated, thus indicating the involvement of a silylpotassium species as the active nucleophilic component.

The thermal sulfenate - Sulfoxide rearrangement: A radical pair mechanism

The thermal reaction of sulfenates (RS-OR), yielding their corresponding sulfoxides (RS(=O)R), was studied experimentally. The first step of the reaction was found to be the formation a radical pair by homolytic cleavage of the carbon-oxygen bond of the sulfenate. The two transient radicals formed then recombine to form the carbon-sulfur bond of the sulfoxide. The thermolysis of cinnamyl-4-nitrobenzenesulfenate has a positive entropy of activation (ΔS? = 6.4 ± 2.0 eu in toluene), characteristic of a dissociative pathway. A normal secondary kinetic isotope effect (kH/kD = 1.19 ± 0.04) was also measured with this substrate. Finally, a trapping experiment allowed the isolation and characterization of a product coming from the coupling of the cinnamyl radical and TEMPO. These studies confirm a mechanism that was proposed earlier based on computational studies. The experimentally determined bond dissociation energy of the carbon-oxygen bond of ~28 kcal·mol-1 is in good agreement with the computed value of ~26 kcal·mol-1. These studies confirm a unique structural feature of the sulfenate moiety, where the weakest bond of the molecule in the ground state is not the heteroatom-heteroatom bond intuitively considered to be the weakest based on the analogy to peroxides or disulfides. Radical stabilizing substituents are expected to have a large effect on the thermal reactivity of sulfenates. Evidence for a competing acid-catalyzed mechanism has also been observed.

Metal-assisted reactions. Part 25. Heterogeneous and homogeneous catalytic transfer hydrogenolysis of allyloxytetrazoles to yield alkenes or alkanes

Transfer hydrogenolysis of 5-allyloxy-1-phenyltetrazoles using either a heterogeneous or a homogeneous palladium catalyst and a hydrogen donor leads to cleavage of the allyloxy C-O bond to yield an alkane or an alkene and 1-phenyltetrazolone, depending on the catalyst used.

Base Catalysed Rearrangements Involving Ylide Intermediates. Part 12. The Preparation and Reactions of 2-Oxidoanilinium Ylides

2-Oxidoanilinium ylides (22) may be prepared from the corresponding quarternary salts (21) by reaction with aqueous sodium hydroxide.The ylides (22) rearrange on heating to give the products (23) of rearrangements which, on the basis of mixing exper