33026-27-6

Upstream product

• 6414-69-3 ethyl 3-iodopropanoate 
• 611-70-1 phenyl isopropyl ketone 
• 6134-72-1 2-benzoyl-4-methylpentanoic acid ethyl ester 
• 539-74-2 Ethyl 3-bromopropionate 
• 87362-59-2 ethyl c-2-hydroxy-3,3-dimethyl-2-phenyl-r-1-cyclobutanecarboxylate 
• 87362-59-2 ethyl t-2-hydroxy-3,3-dimethyl-2-phenyl-r-1-cyclobutanecarboxylate 

Downstream Products

• 2938-68-3 4,4-dimethyl-5-oxo-5-phenylpentanoic acid 
• 20215-66-1 5,5-dimethyl-6-phenyloxan-2-one 
• 87362-59-2 ethyl t-2-hydroxy-3,3-dimethyl-2-phenyl-r-1-cyclobutanecarboxylate 
• 611-70-1 phenyl isopropyl ketone 

Relevant academic research and scientific papers

Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones

We describe a general and versatile approach for the conversion of carboxylic acid amides into their corresponding esters despite the fact that the former are thermodynamically more stable. The transformations are mediated by the coordination of CuI by a chelating entity. The resulting weakening of the amide bond allows for nucleophilic attack by alcoholic hydroxyl functions. The principle is demonstrated for a wide variety of transformations, leading to different kinds of esters and lactones. Due to their high resonance energy, amides are generally very stable towards solvolysis. However, bispicolylamides can be activated for alcoholysis by an unusual metal coordination involving the electron pair of the amide nitrogen. Herein, we widened the scope of the reaction by transforming the amides into a range of esters and lactones.

TYPE II PHOTOREACTIONS OF α-ALKYL β-OXOESTERS. NEIGHBORING GROUP EFFECT ON 1,4-BIRADICAL REACTIONS AND EFFECTIVE INTERNAL FILTER EFFECT BY THE TYPE II PHOTOPRODUCT

The α-alkyl β-oxoesters 1 undergo type II photoreactions.The process of back hydrogen transfer in the 1,4-biradical intermediate to revert to the starting ester is suppressed because of the intramolecular hydrogen bonding between the hydroxyl and carboalkoxyl groups in the biradical intermediate.The hydrogen bonding determines the stereochemistry of 1,4-biradical cyclization.The cyclobutanols having the hydroxyl group cis to the carboalkoxyl group are formed exclusively from the α-alkyl β-oxoesters 1.The enol form of the type II elimination product, the benzoylacetate 2, acts as an effective internal filter for the photoreaction of the α-alkyl β-oxoester 1.

THE NORRISH TYPE II PHOTOREACTION OF BENZOYLVALERATES. STEREOCHEMICAL CONTROL IN 1,4-BIRADICAL CYCLIZATION

The δ- and β-oxoester 1 and 5 underwent the Type II photoreaction to give the stereoisomeric cyclobutanol 2 and 6, respectively; the ethoxycarbonyl group in the esters determines the stereochemistry of 1,4-biradical cyclization.