1240949-52-3

Upstream product

• 502-42-1 cycloheptanone 
• 2158-31-8 cycloheptanone oxime 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones

Carbon-carbon bond formation is among the most important reactions in organic synthesis. Reconstruction of a carbon-carbon bond through ring-opening C-C bond cleavage of a strained carbocycle usually occurs via a thermodynamically preferable pathway. However, carbon-carbon bond formation through thermodynamically less favorable C-C bond cleavage has seldom been documented. Herein, we disclose an unusual C-C bond cleavage of cycloketone oxime esters for [4+1] annulation. Under anaerobic copper(I) catalysis, cycloketone oxime esters underwent regioselective, thermodynamically less favorable radical C-C bond cleavage followed by annulation with enaminothiones; that is, α-thioxo ketene N,S-acetals efficiently affording 2-cyanoalkyl-aminothiophene derivatives. Cyclobutanone, -pentanone, -hexanone, and -heptanone oxime esters could act as the effective C1 building blocks in the annulation reaction. An iminyl radical mechanism is proposed for the rare C-C bond cleavage/[4+1] annulation cascade.

Transition-Metal-Promoted Direct C?H Cyanoalkylation and Cyanoalkoxylation of Internal Alkenes via Radical C?C Bond Cleavage of Cycloketone Oxime Esters

Transition-metal-catalyzed alkyl-Heck-type cross-coupling of olefinic C?H bonds has been a challenge in the C?H activation area. Herein, we report FeCl3-promoted efficient direct C?H cyanoalkylation of internal alkenes, that is, ketene dithioacetals, with cycloketone oxime esters via radical C?C bond cleavage under the redox-neutral conditions. With CuCl2 as the catalyst under a dioxygen atmosphere direct C?H cyanoalkoxylation of the same internal alkenes was achieved. The cyanoalkylated tetrasubstituted alkene products could be diversely transformed to cyanoalkyl-funtionalized N- and S-heterocyclic compounds. The mechanistic studies have revealed that these C?H cyanoalkylation and cyanoalkoxylation reactions proceed through a radical pathway. (Figure presented.).

Sequential [3,3]-Sigmatropic Rearrangement/Nucleophilic Arylation of N -(Benzoyloxy)enamides towards the Preparation of Cyclic β-Aryl-β-amino Alcohols

A new method has been developed for the efficient synthesis of cyclic β-aryl-β-amino alcohol derivatives bearing a tetrasubstituted carbon center via the [3,3]-sigmatropic rearrangement of N-(benzoyl oxy)enamides followed by nucleophilic arylation reactio

O-acyl derivatives of cyclopentanone and cycloheptanone oximes

By acylation of cyclopentanone and cycloheptanone oximes with carboxylic acids anhydrides or chlorides new esters were obtained of cyclopentanone and cycloheptanone oximes and their spectral characteristics were investigated.