16510-81-9

Upstream product

• 67-56-1 methanol 
• 873-49-4 cyclopropylbenzene 
• 75-21-8 oxirane 
• 35364-99-9 α-chlorobenzyl methyl ether 
• 772-00-9 4-phenyl-1,3-dioxane 
• 538-86-3 benzyl methyl ether 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 256229-09-1 3-methoxy-3-phenylpropanal 
• 873-49-4 cyclopropylbenzene 

Relevant academic research and scientific papers

Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents

Different α- and β-substituted aldehydes have been submitted to the catalytic action of almond oxynitrilase (PaHNL), in order to explore the influence of a stereocenter already present in the substrate on the selectivity of this enzyme. The results indicate that naphthyl and alkoxy substituents in the α- and also in the β-position to the aldehyde group significantly influence the stereochemical outcome of the PaHNL-catalyzed transformation.

Metalation of arylmethyl alkyl ethers

Arylmethyl alkyl ethers 1a-11 were metallated with n-BuLi or sec-BuLi in THF at different temperatures, affording α-alkoxy-substituted arylmethyllithium derivatives. At low temperature, the organometallics derived from methyl and isopropyl ethers are suff

Metalation of Arylmethyl Methyl Ethers and Connection with Their Reductive Electrophilic Substitution

Stable α-methoxy arylmethyl carbanions can be generated by metalation of arylmethyl methyl ethers, 1, with n-BuLi in THF at -40 degC, avoiding Wittig rearrengement to the corresponding alkoxides 2.Reaction of these carbanions with various electrophiles afforded the expected products 3 in satisfactory yields.Connection between the metalation procedure and the reductive electrophilic substitution of arylmethyl methyl ethers allowed the transformation of compounds 1 into 2-arylpropanoic acids, 5.

Investigation of the stereochemistry of Fe-Cα bond cleavage when phenylcyclopropane is generated by γ-ionization of stereospecifically deuterated C5H5(CO)2 FeCHDCHDCH(OCH3)C6H5 complexes.

C5H5(CO)2FeCH2CH 2CH(OCH3)C6H5, 4, and stereospecifically deuterium labeled threo-d2-C5H5-(CO) 2FeCHDCHDCH(OCH3)C6H5, 7a,b and erythro-d2-C5H5(CO) 2FeCHDCHDCH(OCH3)C6H5, 8a,b were synthesized. Treatment of compound 4 with trimethylsilyl triflate results in ionization of the γ-methoxy group and formation of phenylcyclopropane in good yields. Ionization of 7a,b gives a 1:1 mixture of cis-2,cis-3-dideuterio- and trans-2,trans-3-dideuterio-r-1-phenylcyclopropane, while ionization of 8a,b gives cis-2,trans-3-dideuterio-r-1-phenylcyclopropane. These results established that the cyclopropane ring is formed by backside attack of electrophilic Cγ on Cα with net inversion of stereochemistry at Cα. These reactions serve as models for the reactions of carbene complexes C5H5(CO)2Fe=CHR+ with alkenes to give cyclopropanes and suggest that in the transfer reactions Fe-Cα is cleaved with inversion.