94374-53-5

Upstream product

• 24806-16-4 allyl p-cymyl ether 
• 107-18-6 allyl alcohol 
• 557-40-4 Allyl ether 
• 98-54-4 para-tert-butylphenol 
• 23473-74-7 2-allyl-4-tert-butylphenol 
• 106-95-6 allyl bromide 

Downstream Products

• 113823-15-7 S-<2,6-bis(3-bromopropyl)-4-(tert-butyl)-1-phenyl> N,N-dimethylthiocarbamate 
• 113823-13-5 S-<2,6-diallyl-4-(tert-butyl)-1-phenyl>N,N-dimethylthiocarbamate 
• 113823-12-4 O-<2,6-diallyl-4-(tert-butyl)-1-phenyl> N,N-dimethylthiocarbamate 
• 113823-14-6 S-<(tert-butyl)-2,6-bis(3-hydroxypropyl)-1-phenyl> N,N-dimethylthiocarbamate 
• 322638-51-7 2-(benzyloxy)-N,N'-bis(4-{[(benzyloxy)carbonyl]amino}butyl)-N,N'-bis(3-{[(benzyloxy)carbonyl]amino}propyl)-5-(tert-butyl)benzene-1,3-bis[propanamide] 
• 322638-58-4 2-(benzyloxy)-N,N'-bis(3-{[(tert-butoxy)carbonyl](4-{[(tert-butoxy)carbonyl]amino}butyl)amino}propyl)-5-(tert-butyl)benzene-1,3-bis[propanamide] 
• 322638-56-2 N,N'-bis{3-[(4-aminobutyl)amino]propyl}-5-(tert-butyl)-2-hydroxybenzene-1,3-bis[propanamide] 
• 364783-94-8 N,N'-bis(4-aminobutyl)-N,N'-bis(3-aminopropyl)-5-(tert-butyl)-2-hydroxybenzene-1,3-bis[propanamide] 
• 322638-61-9 2-(benzyloxy)benzene-1,3,5-tris[propionic acid] 
• 322638-60-8 2-(benzyloxy)benzene-1,3,5-tris[propanol] 
• 322638-50-6 2-(benzyloxy)-5-(tert-butyl)benzene-1,3-bis[propionic acid] 
• 322638-49-3 2-(benzyloxy)-5-(tert-butyl)benzene-1,3-bis[propanol] 
• 322638-48-2 2-(benzyloxy)-5-(tert-butyl)-1,3-di(prop-2-en-1-yl)benzene 
• 20490-22-6 2,4,6-tris(2-propenyl)phenol 

Relevant academic research and scientific papers

Palladium-diphosphine complexes as catalysts for allylations with allyl alcohol

Several palladium complexes with bidentate phosphine ligands were tested for their activity in the O-allylation of phenols with allyl alcohol. The use of C3-bridged bidentate phosphine ligands results in very high selectivity for O-allylation. The reactions do not require stoichiometric amounts of additives to control the chemoselectivity. Especially, catalysts with gem-dialkyl substituted C3-bridged bidentate phosphine ligands perform very well, resulting in a (equilibrium) conversion of ～50% of phenol with a selectivity of 99% for O-allylation. The use of diallyl ether as the allylating agent results in a significant increase in phenol conversion while maintaining high selectivity for O-allylation. Apart from Pd(OAc)2 as catalyst precursor, Pd(dba)2 was also employed, making it possible to use other types of phosphine or phosphite ligands. With the palladium catalytic system not only phenol, but also aliphatic alcohols can be allylated, as well as aromatic and aliphatic amines.

PROCESS FOR THE PREPARATION OF AN ALLYL ARYL ETHER BY CATALYTIC O-ALLYLATON

The invention provides a process for the preparation of an allyl aryl ether comprising the O-allylation of an aromatic hydroxyl containing compound with an allyl source in the presence of a catalyst, wherein the catalyst is a transition metal complex with a bidentate diphosphine ligand, and wherein the bidentate diphosphine ligand has 2 to 4 bridging atoms between the phosphorus atoms and wherein at least one of the bridging atoms is substituted. This invention further provides novel transition metal complexes that may be used in the above process. This invention further provides a process for the preparation of epoxy resins wherein as intermediate use is made of the allyl aryl ethers prepared by the process of the invention.

Immobilization of ruthenium catalysts for allylations with allyl alcohol

[RuCp(PP)]+ complexes active for allylation of alcohols with allyl alcohol as the allylating agent were immobilized on solid supports. Two different immobilization methods have been applied: (1) via electrostatic interactions of the cationic complex on ion-exchange resins, where the anion is present on the support and (2) via a coordination bond with a ligand covalently-bound on the support. Both methods give high yields of immobilized complex through relatively simple procedures. The catalysts immobilized via ionic interactions prove to be able to allylate both 1-octanol and 4-tert-butylphenol with very low leaching of the catalyst, thus forming allyl octyl ether and C-allylated phenol, respectively. The accumulation of water in the highly hydrophilic resin precludes the O-allylation of phenol and also retards the C-allylation reaction. The catalysts immobilized via a coordination bond are not hydrophilic; with these catalysts selective O-allylation of phenols is achieved, with recycling of the catalysts over multiple runs. Leaching of the catalyst from the support is somewhat higher than for the electrostatically-bound catalyst and quarternisation (allylation) of the excess of phosphine groups present on the support plays an important role in the activity of the immobilized catalysts for the allylation reaction.

Cationic ruthenium-cyclopentadienyl-diphosphine complexes as catalysts for the allylation of phenols with allyl alcohol; Relation between structure and catalytic performance in O-vs. C-allylation

A new catalytic method has been investigated to obtain either O-or C-allylated phenolic products using allyl alcohol or diallyl ether as the allyl donor. With the use of new cationic ruthenium(II) complexes as catalyst, both reactions can be performed with good selectivity. Active cationic Ru(II) complexes, having cyclopentadienyl and bidentate phosphine ligands are generated from the corresponding Ru(II) chloride complexes with a silver salt. The structures of three novel (diphosphine)Ru(II)CpCl catalyst precursor complexes are reported. It appears that the structure of the bidentate ligand has a major influence on catalytic activity as well as chemoselectivity. In addition, a strong cocatalytic effect of small amounts of acid is revealed. Model experiments are described that have been used to build a reaction network that explains the origin and evolution in time of both O-allylated and C-allylated phenolic products. Some mechanistic implications of the observed structure vs. performance relation of the [(diphosphine)RuCp]+ complexes and the cocatalytic role of added protons are discussed.

A new one-pot synthetic approach to the highly functionalized (Z)-2-(buta-1,3-dienyl)phenols and 2-methyl-2H-chromenes: Use of amine, ruthenium and base-catalysis

A practical and simple one-pot multi-catalysis process for the synthesis of highly substituted benzo[b]oxepines 5, (Z)-2-(buta-1,3-dienyl)phenols 6 and 2-methyl-2H-chromenes 7 from simple starting materials was achieved for the first time through ring-closing metathesis/base-induced ring opening/[1,7]-sigmatropic hydrogen shift reactions. The synthesis of privileged (Z)-2-(buta-1,3-dienyl)phenols 6 via base-induced ring opening of highly functionalized benzo[b]oxepines 5 is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

Twelve substituted benzofurans were synthesized from their corresponding substituted 1-allyl-2-allyloxybenzenes using ruthenium-mediated C- and O-allyl isomerization followed by ring-closing metathesis.

Synthetic analogues to the spermidine-spermine alkaloid tenuilobine

Naturally occurring spider and wasp toxins are potent inhibitors of glutamate receptors in the central nervous system. They consist of a polyamine backbone and carboxylic acids or amino acids linked by peptide bonds. In some respects, the plant alkaloid t

106. Synthetic Models of the Active Site of Cytochrome P-450. 1st Communication. The Synthesis of a Doubly-Briged Iron(II)-Porphyrin Carrying a Tightly Bound Thiolate Ligand

The doubly-bridged iron(II)-tetraphenylporphyrin dervative 6, carrying a sterically fixed S- ligand in the 'proximal'position and the substrate at the 'distal' site, was synthesized as an enzyme model for cytochrome P-450.Compond 36, the CO com