79574-32-6

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 1885-22-9 bromomalononitrile 
• 109-77-3 malononitrile 

Downstream Products

• 1262235-65-3 C₁₂H₁₂N₂S 
• 61207-11-2 5-(4-methylphenyl)-4,5-dihydro-1,2-oxazole-3-carbonitrile 2-oxide 

Relevant academic research and scientific papers

Stereoselective Construction of Nitrile-Substituted Cyclopropanes from 2-Substituted Ethenesulfonyl Fluorides via Carbon-Sulfur Bond Cleavage

The intermolecular cyclopropanation of 2-aryl and 2-styryl substituted ethenesulfonyl fluorides with active cyano-containing methylene compounds was described. This reaction proceeds via carbon-sulfur bond cleavage under metal-free conditions in up to 99% yield, affording a variety of nitrile-substituted cyclopropanes with high diastereoselectivity. (Figure presented.).

Hypoiodite-mediated cyclopropanation of alkenes

An efficient, transition metal-free procedure for the cyclopropanation of alkenes using malononitrile and the LiI-tBuOCl combination under mild reaction conditions is described. The reaction mechanism most likely involves tBuOI generated in situ from LiI and tBuOCl. The utility of this new methodology has been demonstrated by the synthesis of a potential HIV-1 RT inhibitor. An efficient, transition-metal-free procedure for the cyclopropanation of alkenes using malononitrile and the LiI/tBuOCl combination under mild reaction conditions is described. The reaction mechanism most likely involves tBuOI generated in situ from LiI and tBuOCl. The utility of this new methodology has been demonstrated by the synthesis of a potential HIV-1 RT inhibitor (see scheme).

Hypoiodite-mediated catalytic cyclopropanation of alkenes with malononitrile

An efficient synthetic procedure for di-cyano-cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert-butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl-substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed,.

Hypervalent iodine(iii)-mediated cyclopropa(e)nation of alkenes/alkynes under mild conditions

Hypervalent iodine(iii)-mediated dioxygenation and diamination of alkenes have been previously developed. In this study, the potential application of hypervalent iodine(iii) reagent was successfully extended to the dialkylation and cyclopropa(e)nation of

Synthesis of functionalized dihydrothiophenes from doubly activated cyclopropanes using tetrathiomolybdate as the sulfur transfer reagent

A number of doubly activated cyclopropanes were synthesized starting from various substituted bromosulfonium bromides in good yield. Regioselective ring-opening of cyclopropanes with tetrathiomolybdate as the sulfur transfer reagent gave dihydrothiophenes

Synthesis and electronic effect of the substituents on anionic ring- opening polymerization of para-substituted phenyl cyclopropanes

As an extension of studies in the anionic polymerization of activated cyclopropanes with electronically push-pull substituents, p-substituted phenylcyclopropane-1,1-dicarbonitriles having Me0, Me, H, Cl, and NO2 as substituents were prepared. The electronic effects of substituents upon the ring-opening reaction during anionic polymerizations were examined by determining the rate constants of polymerizations, conversions and molecular weights of the resulting polymers. The rate constants of polymerization(k(p)) in DMSO by 2 mole% cyanide ion at 35 °C were p-Me0=0.45, p-Me=0.14, p- H=0.07, p-Cl=0.06 and p-NO2=0.01 litter/mole.sec, and the rate constants of polymerization in DMSO by 5 mole% pyridine at 35 °C were p-Me0=048, p- Cl=7.6 x 10-3 and p-NO2=1.64 x 10-3 liter/mole.sec., respectively. The electronic effect exerted by substituents were well consistent with the Hammett relationship(log k/k(o)=σ ρ) when Brown's σ+ constants were used. The reaction sensitivity constants(ρ) obtained from cyanide ion initiator were -1.0 and -0.94 for pyridine initiation. These results indicate that the anionic ring-opening polymerization of p-substituted phenylcyclopropanes is carried out via highly conjugated zwitterionic transition state in the ring opening reaction. Furthermore, in the case of the polymerization initiated by pyridine or triethylamine, the formation of macrozwitterion during polymerization is a feasible mechanism.

A New Synthetic Route to Electrophilic Cyclopropane Derivatives from Olefins

1,1-Bis(alkoxycarbonyl)-, 1-alkoxycarbonyl-1-cyano-, and 1,1-dicyanocyclopropane derivatives were obtained in 10-99percent yields by the reaction of Br2C(COOR)2, Br2C(CN)(COOR), and KBr4, respectively, with olefins and Cu2Br2 in dimethyl sulfox