98122-97-5

Upstream product

• 591-51-5 phenyllithium 
• 5222-73-1 3,4-dimethoxy-3-cyclobutene-1,2-dione 
• 108-86-1 bromobenzene 

Downstream Products

• 6956-96-3 2,3-dimethoxy-1,4-naphthoquinone 
• 711-78-4 3-methoxy-4-phenylcyclobutenedione 
• 145011-60-5 2,3-dimethoxy-1,4-dihydroxynaphthalene 
• 144790-91-0 1-hydroxy-1-(1-hexynyl)-2-phenyl-3-n-butyl-4,4-dimethoxy-2-cyclobutene 
• 144790-88-5 1-hydroxy-1-(1-hexynyl)-2-phenyl-3-methyl-4,4-dimethoxy-2-cyclobutene 
• 144790-90-9 1-hydroxy-1-ethenyl-2-phenyl-3-n-butyl-4,4-dimethoxy-2-cyclobutene 
• 144790-85-2 2-phenyl-3-butyl-4,4-dimethoxy-2-cyclobuten-1-one 
• 144790-92-1 1-hydroxy-1,2-diphenyl-3-methyl-4,4-dimethoxy-2-cyclobutene 
• 144790-97-6 4-Hydroxy-2-methyl-3,4-diphenyl-cyclobut-2-enone 
• 144790-84-1 2-phenyl-3-methyl-4,4-dimethoxy-2-cyclobuten-1-one 
• 144790-80-7 2-phenyl-3,4,4-trimethoxy-2-cyclobuten-1-one 

Relevant academic research and scientific papers

Mn(III)-based oxidative radical ring-expansion reaction using squarate derivatives: Selective synthesis of bis(butenolide)s and the acetate monomers

The Mn(III)-based oxidation of phenyl- and alkyl-substituted hydroxycyclobutenones selectively produced the bis(butenolide)s or the acetate monomers via the 5-endo radical cyclization depending upon the concentration of the reaction. A similar reaction of hydroxycyclobutenones bearing an alkenyl and alkynyl substituent did not produce any bis(butenolide)s or acetate monomers, but the 5-exo and 6-endo radical cyclization products including the unsaturated group. The oxidation of the hydroxycyclobutenones having an unsaturated substituent in the presence of alkenes afforded radical coupling products during the 5-exo radical cyclization. The reaction details, structure determination of the products, and the mechanism for the formation of the products are described.

An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements

Go with the flow: 4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in th

New insights into cyclobutenone rearrangements: A total synthesis of the natural ROS-generating anti-cancer agent cribrostatin 6

Aryl- and heteroarylcyclobutenone rearrangements proceed in excellent yield under continuous-flow conditions. The former shows a Hammett correlation with σI providing strong evidence that electrocyclisation is the rate-determining step and has a late transition state. The reaction has been modelled by using DFT and CCSD(T) methods, with the latter giving excellent correlation with the experimental rate constant. A short and efficient total synthesis of cribrostatin 6, an anti-neoplastic and anti-microbial agent, provides a topical demonstration of the value of this method.

A Potentially General Regiospecific Synthesis of Substituted Quinones from Dimethyl Squarate

A potentially general regiospecific synthesis of benzo- and naphthoquinones is described.This method starts with dimethyl squarate (1) which is converted to the cyclobutenone ketal 3 upon sequential treatment with an organolithium reagent and then BF3 etherate or TFAA in THF/methanol.Treatment of these with a second lithium reagent followed by hydrolysis gives the cyclobutenones 5.Addition of an alkynyl-, alkenyl- or aryllithium agent to 5 followed by hydrolysis of the ketal linkage gives the corresponding 4-alkynyl-, 4-alkenyl- or 4-aryl-4-hydroxycyclobutenones7 - 9, and these readily rearrange to the respective quinones or hydroquinones upon thermolysis in refluxing benzene.In a similar fashion, 15 was employed as a reagent to prepare mono- and disubstituted hydroquinones and quinones.

PHOTOLYSIS OF 4-SUBSTITUTED-4-HYDROXY-3-CYCLOBUTEN-1-ONES: A NEW ROUTE TO BUTENOLIDES FROM 4-HYDROXYCYCLOBUTENONES

Photolysis of 4-substituted-4-hydroxy-3-cyclobuten-1-ones undergo electrocyclic ring opening followed by ring closure to provide butenolide products.This transformation is envisaged to involve a stereoselective disrotatory electrocyclic ring opening to co

Synthesis of 4-Substituted-3-alkoxy-3-cyclobutene-1,2-diones

4-Substituted-3-alkoxycyclobutenediones 3 were obtained from dialkoxycyclobutenediones (dialkyl squarates) 1 by the addition of organolithium reagents followed by hydrolysis of the resulting hydroxycyclobutenone 2.A particularly useful one-pot procedure i

General Regiospecific Synthesis of Annulated Quinones

A general regiospecific synthesis of annulated hydroquinones/quinones is presented.This specifically involves the thermal rearrangement of the 4-aryl-4-hydroxycyclobutenones 1a-k to the corresponding annulated hydroquinones.The synthetic scope and mechani

REACTIVITY OF ORGANO LITHIUM REAGENTS ON DIMETHYL SQUARATE: A 1,2-ADDITION PROCESS LEADING TO NEW 1-HYDROXY-3,4 DIMETHOXY 3-CYCLOBUTENONE

Lithium reagents react with dimethylsquarate at the carbonyl group according to a 1,2-addition process, leading to new 2-hydroxy-3,4 dimethoxy-3 cyclobutenone.