32708-26-2

Upstream product

• 24017-92-3 2'-acetyl-[1,1'-biphenyl]-2-carboxylic acid 
• 24017-91-2 2'-acetyl-[1,1'-biphenyl]-2-carboxylic acid methyl ester 
• 32708-28-4 3-hydroxydibenzotropnone 
• 32807-95-7 7-chloro-dibenzo[a,c]cyclohepten-5-one 
• 32708-40-0 7-morpholin-4-yl-dibenzo[a,c]cyclohepten-5-one 
• 84-11-7 9,10-phenanthrenequinone 

Relevant academic research and scientific papers

Reaction of a moderately stabilized bismuthonium ylide with 1,2-dicarbonyl compounds. A novel ring enlargement of ortho-quinones to 3-hydroxytropones

Triphenylbismuthonium 2-oxoalkylide 2, generated in situ from salt 1 in THF at low temperature, readily reacts with 1,2-dicarbonyl compounds 3 to give 2,3-diacyloxiranes 4 or 2-acyl-3-hydroxytropones 5 depending on the structure of the electrophiles invol

Reactions of triphenylbismuthonium 2-oxoalkylides with 1,2-dicarbonyl compounds

Triphenylbismuthonium 2-oxoalkylides 2, generated in situ from bismuthonium salts 1 and a base in THF at low temperature, react with α-keto esters 3 and α-diketones 6 to give oxiranes 4 or 7 and/or O-aroyl enolates of unsymmetrical β-diketones 8, depending on the structures of substrates. Similar treatment of 2 with o-quinones 10 results in the ring expansion to 2-acyl-3-hydroxytropones 11. The enolates 8 and tropones 11 are most likely to be formed via the 1,2-carbon-to-oxygen and carbon-to-carbon migrations of the acyl group, respectively, both under simultaneous elimination of the triphenylbismuthonio group as bismuthine 5. Tropone 11c readily condenses with hydrazine hydrate to give a functionalized pyrazole 18.