70106-27-3

Upstream product

• 144453-17-8 1-(phenylthio)cyclopropyl-1-(4-methoxyphenyl)-methanol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 16510-27-3 1-(cyclopropylmethyl)-4-methoxybenzene 
• 55088-84-1 4-methoxybenzylidenecyclopropane 
• 87639-43-8 4-(4-methoxyphenyl)but-3-yn-1-yl 4-methylbenzenesulfonate 
• 124708-62-9 4-methoxyphenyl(1-methoxycycloprop-1-yl)methanol 

Downstream Products

• 70106-32-0 1,1,2,2,3,3,4,4,4-Nonafluoro-butane-1-sulfonic acid 2-(4-methoxy-phenyl)-cyclobut-1-enyl ester 
• 61349-69-7 (±)-2-(4-methoxyphenyl)cyclopentan-1-one 
• 116526-34-2 3-(4-methoxyphenyl)cyclopentanone 
• 1225505-27-0 4-hydroxy-4-(4-methoxyphenyl)butanenitrile 

Relevant academic research and scientific papers

Iron-Catalyzed Ring Expansion of Cyclobutanols for the Synthesis of 1-Pyrrolines by Using MsONH3OTf

The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONH3OTf) has been developed. This one-pot procedure achieves C–N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthes

Synthesis of 2-Substituted Cyclobutanones by a Suzuki Reaction and Dephosphorylation Sequence

We report a novel process for the preparation of 2-substituted cyclobutanones. Such a method relies on the cross-coupling reaction of bromocyclobutenyl diethyl phosphate with either boronic acids or organozinc reagents. Dephosphorylation of the prepared 2-substituted cyclobutenyl phosphates affords 2-substituted cyclobutanones. We observed that the course of the dephosphorylation reaction depends on the properties of the substituents found on the cyclobutene nucleus. The presence of groups capable of stabilizing the negative charge is necessary for ring opening of cyclobutanones. The scope of the reported process for the preparation of 2-substituted cyclobutanones has also been extended to the preparation of cyclobutenyl sulfides.

Visible light-induced palladium-catalyzed ring opening β-H elimination and addition of cyclobutanone oxime esters

A palladium catalyst under visible light irradiation activates cyclobutanone oxime ester through single electron transfer to induce radical ring opening to generate hybrid cyanoalkyl Pd(i) radical species. Hybrid cyanoalkyl Pd(i) radical species can undergo either β-H elimination to deliver (E)-4-arylbut-3-enenitrile or undergo radical addition with silyl enol ether and enamide to generate δ-cyano ketones. A dual ligand system composed of two phosphine ligands is essential for the high reactivity.

Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

A chemodivergent copper-catalyzed ring opening of cycloketone oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of γ- and δ-acyloxylated, alkoxylated, and hydroxylated nitriles while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxime also proceeded well under the established conditions.

Synthesis of benzodiquinanes via tandem palladium-catalyzed semipinacol rearrangement and direct arylation

A palladium-catalyzed tandem semipinacol rearrangement/direct arylation reaction using α-aryl isopropenyl-tert-cyclobutanols has been developed. This reaction gives access to benzodiquinanes in moderate to good yields and tolerates alkyl-, alkoxy-, and ha

Catalytic and regioselective ring expansion of arylcyclobutanones with trimethylsilyldiazomethane. Ligand-dependent entry to β-ketosilane or enolsilane adducts

Divergent reactivity is uncovered in the homologation of arylcyclobutanones with trimethylsilyldiazomethane. With Sc(OTf)3 as catalyst, enolsilanes are obtained with a high preference for methylene migration. By contrast, Sc(hfac)3 g

EFFICIENT SYNTHESYS OF 2-VINYLCYCLOBUTANONES BY THE REARRANGEMENT OF 1-METHOXY-1-CYCLOPROPYLCARBINOLS UNDER NEUTRAL CONDITIONS

A common synthesis of cyclobutanones involves the rearrangement of 1-alkoxy- or 1-(phenylthio)cyclopropylcarbinols under acidic conditions.We report that the synthetically useful 2-vinylcyclobutanones can be prepared in good yield in the absence of proton

Vinyl Cations. 41. Influence of 4-Aryl and 4-Alkyl Substituents on the ?-Route Solvolyses of Homopropargyl Esters

The four 4-substituted-homopropargyl tosylates and triflates 6b-e (R=phenyl, p-tolyl, anisyl, and cyclopropyl) have been synthesized and solvolyzed under various conditions, as have 2-cyclopropyl-1-cyclobutenyl triflate (11-OTf) and nonaflate (11-ONf).In addition, the solvolyses of pent-3-yn-1-yl tosylate (6a-OTs, R=methyl) and triflate (prepared previously) are reported.The ratios of C-3 ring to C-4 ring 3 ring/C4ring)> products are recorded for the reactions in various solvents.As expected, ring closure (kΔ) increases and solvent displacement (kS, SN2) decreases with decreasing nucleophilicity of solvent.Temperature effects are noted for the sovolyses of tosylates 6a-e in 100percent TFE buffered with Na2CO3 in which kΔ increases with increasing temperature.The result is explained by decomposition of the intimate ion pair with temperature, whereupon elimination to the enyne becomes smaller and ring closure (kΔ) increases at the expense of elimination.The possibility of intervention of nonclassical vinyl cations is discussed, as are other mechanistic implications.

A SYNTHESIS OF 2-VINYLCYCLOBUTANONES USING 1-METHOXYCYCLOPROYLLITHIUM REAGENTS

A facile synthesis of 2-vinylcyclobutanones consists of reductive lithiation of 1-phenylthio-1-methoxycyclopropanes, addition of enals or enones to the resulting α-lithioethers, and acid catalyzed rearrangement of the allylic alcohols thus produced.