344304-35-4

Upstream product

• 13138-21-1 diazoacetonitrile 
• 4747-13-1 α-methoxystyrene 
• 82736-62-7 methoxy(phenyl)diazirine 
• 107-13-1 acrylonitrile 
• 59526-67-9 methoxyphenylcarbene 
• 4222-25-7 3-bromo-3-phenyl-3H-diazirine 

Downstream Products

• 83832-69-3 4,4-dimethoxy-4-phenylbutanenitrile 
• 83832-67-1 4-methoxy-4-phenyl-3-butenenitrile 
• 83832-67-1 4-methoxy-4-phenyl-3-butenenitrile 

Relevant academic research and scientific papers

Synthesis of donor-acceptor alkynylcyclopropanes by diastereoselective cyclopropanation of electron-deficient alkenes with alkoxyalkynyl fischer carbene complexes

The reaction of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes (FCCs) represents a straightforward route to a new type of captodative (donor-acceptor) alkynylcyclopropanes, which have been prepared in moderate to high yields and i

THE CARBENE COMPLEX ROUTE TO DONOR-ACCEPTOR-SUBSTITUTED CYCLOPROPANES

A variety of donor-acceptor-substituted cyclopropanes can be synthesized starting from electron deficient olefins in preparatively usefull yields employing Fischer carbene complexes as donor-carbene source.

CHLOROACRYLONITRILE, A DETECTOR SUBSTRATE FOR CARBENE NUCLEOPHILICITY; APPLICATIONS TO PHENYLHALOCABENES

α-Chloroacrylonitrile is an excellent substrate for nucleophilic and ambiphilic carbenes; its use permits visualization of the latent ambiphilic properties of the phenylhalocarbenes.

Absolute Rate and Philicity Studies of Methoxyphenylcarbene. An Extended Range for Carbenic Ambiphilicity

Methoxyphenylcarbene (MeOCPh) was generated by photolysis (-10 deg C) or thermolysis (25, 45 deg C) of 3-methoxy-3-phenyldiazirine and added to six alkenes, affording the corresponding cyclopropanes.The substrates and their relative reactivities toward th

Rearrangements of Oxocyclopropanecarboxylate Esters to Vinyl Ethers. Disparate Behavior of Transition-Metal Catalysts

Diverse transition-metal compounds catalyze the conversion of 2-alkoxycyclopropanecarboxylate esters to derivative vinyl ethers in high yield under mild conditions.With 2, PtCl2*2PhCN, or 2, structural rearrangement occurs with concurrent epimerization of the reactant cyclopropane compound, and identical isomeric mixtures of vinyl ethers are formed from either of the two stereoisomeric cyclopropane reactants.Rhodium(II) acetate catalyzed reactions occur at higher temperatures than those required with 2, epimerization of the (Z)-cyclopropane isomer, but not the E isomer, is observed, and individual stereoisomeric cyclopropane reactants produce different isomeric mixtures of vinyl ether products.The characteristics of copper bronze and copper(I) chloride catalyzed reactions are generally similar to those of Rh2(OAc)4, except with ethyl 2-methoxy-2-vinylcyclopropanecarboxylate, which undergoes rearrangement to the isomeric ethyl 3-methoxycyclopentenecarboxylates in the presence of these copper catalysts.Participation by the carbethoxy group in rhodium(I)-, platinum (II)-, and ruthenium(II)-catalyzed reactions is indicated in results from comparative reactions with nitrile and sulfone derivatives, and the mechanistic involvement of a six-membered ring metallocycle is suggested.In rhodium(II)- and copper-catalyzed reactions, metallocyclobutane intermediates are proposed to account for their contrasting results.Catalytic rearrangement of (allyloxy)cyclopropanecarboxylate esters affords 3-allyl-4-oxoalkanoate esters in good yield by a synthetic coupling of the oxocyclopropane-vinyl ether and Claisen rearrangement transformations.