18276-79-4

Upstream product

• 31827-94-8 2-bromo-1-(4-iodophenyl)ethanone 
• 122-52-1 triethyl phosphite 
• 4209-04-5 2-chloro-1-(4-iodophenyl)ethan-1-one 
• 13329-40-3 4-Iodoacetophenone 
• 814-49-3 diethyl chlorophosphate 

Relevant academic research and scientific papers

Selective Alkenylation and Hydroalkenylation of Enol Phosphates through Direct C-H Functionalization

An efficient and selective Rh-catalyzed direct C-H functionalization reaction of enol phosphates was developed. The method is applicable to a variety of coupling partners, including activated alkenes, alkynes, and allenes, and leads to the formation of various valuable alkenylated and hydroalkenylated enol phosphates through the action of the phosphate directing group. The versatility and utility of the coupling products were demonstrated through further transformations into synthetically useful building blocks. P points the way: A direct C-H functionalization of enol phosphates was developed. The method is applicable to a variety of coupling partners, including activated alkenes, alkynes, and allenes, and it leads to the formation of alkenylated and hydroalkenylated enol phosphates through the action of the phosphate directing group. The utility of the coupling products are demonstrated by further transformations into synthetically useful building blocks.

Mechanism of the Reaction of Trialkyl Phosphites with α-Halogenoacetophenones in Alcoholic Solvents

Second-order rate constants and activation parameters have been determined for the reactions of trialkyl phosphites in alcoholic media with α-chloro- or α-bromo-acetophenones having various substituents in the benzene ring (3,4-Me2, 4-Me, H, 4-Cl, and 4-I).Linear Hammett plots are consistent with the involvement of a common first intermediate in the rate-determining stage, leading to the formation of vinyl phosphate, α-hydroxyphosphonate, and acetophenone.The results provide the first kinetic evidence in support of the initial formation of the previously suggested betaine as a common intermediate in alcoholic solution.Further reaction then involves rearrangement to give the vinyloxyphosphonium species (and hence the Perkow product) or protonation followed by dealkylation to give the α-hydroxyphosphonate.Evidence for the possible formation of dehalogenated ketone via solvolysis of the α-hydroxyphosphonium intermediate is also presented.