100511-39-5Relevant academic research and scientific papers
Photo-mediated [1, 3]-Carbonyl shift of β-Ketocarbonyls
Zhang, Wenzhao,Li, Yao,Luo, Sanzhong
, (2020/04/29)
An organic amine mediated photolytic [1,3]-benzoyl migration of β-benzoyl carbonyl compounds was reported. This migration was achieved by Norrish-Yang cyclization and retro-aldol reaction under black light (365 nm) or visible light irradiation. This photolytic protocol provides an alternative approach to the synthesis of 1,5-dicarbonyl compounds. By chiral primary amine catalysis, a kinetic resolution was also developed to afford enantioenriched 1,5-dicarbonyls.
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
Hasegawa, Tadashi,Arata, Yoshiaki,Endoh, Masaru,Yoshioka, Michikazu
, p. 1667 - 1674 (2007/10/02)
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.
