144790-85-2

Upstream product

• 591-51-5 phenyllithium 
• 98122-97-5 2,3-dimethoxy-4-hydroxy-4-phenyl-2-cyclobuten-1-one 
• 5222-73-1 3,4-dimethoxy-3-cyclobutene-1,2-dione 
• 144790-80-7 2-phenyl-3,4,4-trimethoxy-2-cyclobuten-1-one 

Downstream Products

• 144790-90-9 1-hydroxy-1-ethenyl-2-phenyl-3-n-butyl-4,4-dimethoxy-2-cyclobutene 
• 144790-91-0 1-hydroxy-1-(1-hexynyl)-2-phenyl-3-n-butyl-4,4-dimethoxy-2-cyclobutene 

Relevant academic research and scientific papers

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.