73481-93-3

Upstream product

• 98-87-3 benzylidene dichloride 
• 79695-50-4 potassium salt of E-crotylalcohol 
• 100-52-7 benzaldehyde 
• 4784-77-4 (E/Z)-crotyl bromide 
• 75851-76-2 1-phenylpent-3-en-1-ol 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 100-47-0 benzonitrile 
• 74087-85-7 3,3-dimethyldioxirane 
• 1588-56-3 trans-2-phenyl-1-ethylcyclopropane 
• 6704-77-4 2-phenyl-3-(1-propenyl)oxirane 

Downstream Products

• 1158843-64-1 2-(3-methyloxiran-2-yl)-1-phenylethanone 
• 76620-27-4 4-methyl-N'-((1E,3Z)-1-phenylpent-3-en-1-ylidene)benzenesulfonohydrazide 
• 75851-76-2 (Z)-1-phenyl-3-penten-1-ol 
• 75851-77-3 (E)-1-phenyl-3-penten-1-ol 

Relevant academic research and scientific papers

Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane

Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range ofZ-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific

Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary or Two Vicinal Stereocenters

We have developed an asymmetric aza-Wacker-type cyclization of N-Ts hydrazine-tethered tetrasubstituted olefins, affording optically active pyrazolines bearing chiral tetrasubstituted carbon stereocenters. This reaction is tolerant to a broad range of substrates under mild reaction conditions, giving the desired chiral products with high enantioselectivities. Generation of two vicinal stereocenters on the C=C double bonds was also achieved with high selectivities, a process which has been rarely studied for Wacker-type reactions. A mechanistic study revealed that this aza-Wacker-type cyclization undergoes a syn-aminopalladation process. It was also found that for substrates bearing two linear alkyl substituents on the outer carbon atom of the olefin, both of which are larger than a methyl group, the alkyl substituent that is cis to the intranucleophilic group participates more readily in β-hydride elimination. When one of the two alkyl substituents on the outer carbon atom of the olefin is a methyl group, β-hydride elimination proceeds selectively at the methylene side, thus both diastereomers can be prepared via switching the configuration of the olefin. Furthermore, the product can be converted to a pharmaceutical compound in high yields over three steps.

Stereoselective preparation of 3-alkanoylprop-2-en-1-ol derivatives

3-Alkanoylprop-2-en-1-ol derivatives were prepared stereoselectively by ring-opening reaction of β,γ-epoxyketone with amines. Georg Thieme Verlag Stuttgart.

Diene-titanium complexes as synthetic intermediates for the construction of three or five-membered carbocycles

It has been shown that diene-titanium complexes exhibit substrate-dependent 1,2- or 1,4-dicarbanion reactivity. On this basis, 3-cyclopen-tenylamines and spiro-vinylcyclopropane lactams were easily prepared by using homoallylic Grignard reagents, Ti(O-i-P

Dimethyldioxirane hydroxylation of a hypersensitive radical probe: Supporting evidence for an oxene insertion pathway

Dimethyldioxirane oxidation of the hypersensitive radical probe (trans- 2-phenylcyclopropyl)ethane gave non-rearranged hydroxylation products consistent with an oxene insertion mechanism for the reaction.

Oxyanionic Substituent Effect on the C-H Insertion of Carbenes. Reaction of Alkoxides with Dichlorocarbene and Chlorophenylcarbene

The lithium alkoxides of benzylic, allylic, and simple alkyl alcohols were allowed to react with chloroform in the presence of t-BuOLi in THF-hexane to give, in 32-91percent yields, dichloromethylcarbinols, which were produced by the insertion of dichlorocarbene into the α C-H bond of alkoxides but not by the Wittig rearrangement of carbanions of alkyl dichloromethyl ethers.The enhanced reactivity toward dichlorocarbene of the α C-H bond of alkoxides was clearly demonstrated by the high selectivity of the insertion.The potassium alkoxides of a series of analogous alcohols reacted analogously with benzal chloride in the presence of t-BuOK in THF to give the corresponding substituted oxiranes (16-79percent); e.g., the reaction of potassium benzyl oxide gave 2,3-diphenyloxirane (79percent) as a mixture of stereoisomers (trans:cis = 1.0).With 2-phenethoxide, n-octyl oxide, or 2-methoxyethoxide, the corresponding dialkyl acetals of benzaldehyde were also formed in 9, 6, and 6percent yield, respectively, and their formation is explained in terms of nucleophilic attack of alkoxide on chlorophenylcarbene.With trans-crotyl oxide or 2-phenetoxide, 1,3-diphenylpropan-1-one(33percent) and 1-phenylpent-3-en-1-one (6percent) were produced, respectively, as byproducts through the isomerization of the primary product oxiranes.Oxiranes were produced by the insertion of chlorophenylcarbene into the α C-H bond of alkoxides followed by the cyclization of the intermediate 1-substituted 2-chloro-2-phenethyl alkoxide.These reactions provide us with new preparative methods of synthetically useful dichloromethyl carbinols and oxiranes.