87971-35-5

Upstream product

• 17230-31-8 2-methoxy-1,3-dioxane 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 33603-87-1 β-chlorocinnamaldehyde 
• 504-63-2 trimethyleneglycol 
• 141022-80-2 (E)-1-(1',3'-dioxan-2'-yl)-2-phenylethene 
• 768-03-6 Phenyl vinyl ketone 

Relevant academic research and scientific papers

Palladium(II)-Catalyzed Acetalization of Terminal Olefins Bearing Electron-Withdrawing Substituents with Optically Active Diols

Terminal olefins bearing electron-withdrawing substituents such as CH2=CHCOR (R=Ph, Me, t-Bu), CH2=CHCOOMe, and CH2=CHCN are regioselectively acetalized at the terminal carbon (C1) by diols in the presence of PdCl2 (0.1 equiv) and CuCl (1 equiv) in DME at 50 deg C under an atmosphere of O2 (1 atm).The use of optically active (R,R)-2,4-pentanediol (4) gives homochiral cyclic acetals of aldehyde precursors in good yields.The acetalization of CH2=CHCOR is accompanied by the formation of Michael-type adducts such as 3a (R=Ph).However, of importance is that their formation can be prevented by the use of Na2HPO4 as an additive.Although in an early stage of the reaction of CD2=CHPh with 4, a statistical d scrambling of the starting olefin occurs, no such scrambling is observed with CD2=CHCOPh.Additionally, the acetalization of CD2=CHCOPh with 4 results in 1,2 deuterium migration, together with 25percent d loss.These results are accounted for by the reaction pathways involving oxypalladation, Pd-H elimination, and subsequent ring closure giving enol ether.A catalytic cycle involving the oxygenation of Pd-H species with molecular oxygen is proposed.

Metal-free, PTSA catalyzed facile synthesis of β-ketoacetal from β-chlorocinnamaldehyde

A toluene solution of β-chlorocinnamaldehyde and dihydroxy alcohols in the catalytic presence of para-toluenesulphonic acid (PTSA) yield the β-ketoacetal in good to outstanding amount. The catalyst (PTSA), first selectively protect the aldehydic group to form the β-chloroacetal and the subsequent dechlorination by H2O result the β-ketoacetal. Significant transformation was achieved with electron donating substituent attached at the para-position of cinnamaldehyde. The selective formation of β-keto-1,3-acetal was also obtained with a mixture of 1, 2- and 1, 3- diol. The present reaction consists of a metal-free, economical, robustly feasible, sizeable functional group tolerance and high yield properties. Moreover, the use of different dihydroxy alcohols made this process more benign and valuable towards the metal-free development of ketones. First, of its kind, a rare and unusual multitasking nature of PTSA is observed.

The Stereochemistry of Organometallic Compounds. XXXIX. Hydroformylation of Alkenes Containing Sulfur and Oxygen Substituents: a Potential Route to 1,4-Dialdehydes

Rhodium-catalysed hydroformylation of a series of unsaturated thioethers, dithians, dioxans and dioxolans has been shown to give aldehydes in very good yield.The regioselectivity in some cases appears to be influenced by coordination between the rhodium c

Catalysis of Pd(II)-catalyzed acetalization of alkenes with diols

Alkenes bearing electron-withdrawing substituents are catalytically acetalized with 1,3-propanediol only by the use of PdCl2(MeCN)2 catalyst under O2 atmosphere. When a combination of BiCl3 and LiCl is used as co-catalyst, the acetalization proceeds effectively. These results indicate that a hydroperoxopalladium(II) species is most likely an active catalyst in the present reaction.

Functionalizations with Silyl Enol Ethers, V. - Zinc Chloride-mediated Alkoxyalkylation of Trimethylsilyl Enol Ethers with 2-Alkoxy-1,3-dioxanes to α-Dioxanyl Ketones

The synthetic potential of Lewis acid-mediated alkoxyalkylation of silyl enol ethers with some SN1-active 2-alkoxy-1,3-dioxanes 1, 2 for the preparation of α-dioxanyl ketones 6 is described.

Palladium(II)-catalysed Acetalization of Terminal Olefins Bearing Electron-withdrawing Substituents with 1,3- and 1,2-Diols

Treatment of terminal olefins bearing electron-withdrawing groups with (R,R)-pentane-2,4-diol (2) in the presence of PdCl2-CuCl-O2 in 1,2-dimethoxyethane gives cyclic acetals such as (3) and (12b) via attack at the terminal carbon atom; the corresponding acetals are similarly formed from propane-1,3-diol (5) and ethylene glycol (8).