88795-76-0

Upstream product

• 615-83-8 2-bromo-pentanoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 118688-48-5 ethyl ester of the 2-chlorovaleric acid 
• 5459-35-8 2-bromo-acrylic acid ethyl ester 
• 557-20-0 diethylzinc 

Downstream Products

• 6683-92-7 1-phenylpentan-2-one 
• 344886-85-7 2-propyl-3-phenyl-2,3-epoxypropionic acid 

Relevant academic research and scientific papers

Theoretical investigation of the reaction of dialkylzincs with α-alkoxycarbonyl radicals. Evaluation of α-bromoacrylates as radical acceptors in radical-polar crossover processes

The evaluation of ethyl α-bromoacrylate as radical acceptor in dialkylzinc radical-polar cascades addresses the question of the parameters controlling homolytic substitution at zinc by α-alcoxycarbonyl radicals. Under non-degassed medium ethyl α-bromoacrylate reacts with diethylzinc to give a bromocyclopropane. The reaction involves successively radical addition, SH2 at zinc, conjugate addition of the resulting enolate to the electrophilic substrate and ring closure. Theoretical calculations were performed to get a better insight into the detailed mechanism. They highlight the impact of zinc(II) chelation on the formal SH2 step. Additional experiments performed in the presence of other electrophiles-aldehydes and acylsilanes-are discussed.

GENERAL RELATIONSHIPS IN THE OPENING OF THE OXIRANE RING DURING CLEAVAGE OF GLYCIDIC ACIDS

By investigation of the decarboxylation of 2,3-epoxy derivatives of acids with various structures it was shown that contrary to the existing theory about the essential opening of the β (C-O) bond in the oxirane ring there are many structural types of 2,3-epoxypropionic acids, in which opening of the α (C-O) bond in the oxirane ring occurs during decarboxylation.It was also shown that these two possible reaction paths can also arise during the decarboxylation of one 2,3-epoxypropionic acid.On the basis of the obtained data a general relationship is developed for theopening of the oxirane ring during the decarboxylation of 2,3-epoxypropionic acids with any structure, and this makes it possible to predict the structure of the obtained carbonyl compound.