70871-46-4

Usage

InChI:InChI=1/C13H14O2/c1-9-5-7-10(8-6-9)11-3-2-4-12(14)13(11)15/h5-8,15H,2-4H2,1H3

Upstream product

• 10316-66-2 2-hydroxy-2-cyclohexen-1-one 
• 106-38-7 para-bromotoluene 
• 765-87-7 cyclohexane-1,2-dione 
• 6705-49-3 7-oxabicyclo[4.1.0]heptan-2-one 

Downstream Products

• 116943-49-8 Toluene-4-sulfonic acid 6-oxo-2-p-tolyl-cyclohex-1-enyl ester 
• 116962-33-5 4'-Methyl-biphenyl-2,3-diol 

Relevant academic research and scientific papers

A one-pot isomerization-arylation of 2,3-epoxycyclohexanone under controlled microwave heating

A fast one-pot method has been developed for the direct preparation of 3-aryl-1,2-cyclohexanediones from 2,3-epoxycyclohexanone via a microwave-assisted tandem epoxy ketone isomerization-Heck arylation reaction. The preparative microwave-assisted reactions were performed preferentially in 50% aqueous poly(ethylene glycol) utilizing sodium acetate as the base. Within 5-30 min of directed microwave heating, employing less than 0.05 mol % of palladium acetate and no phosphine ligand, up to 72% yield of C3-arylated dike tones was isolated in an overall environmentally benign process. On the basis of the chemical reactivity of proposed intermediates, a reaction pathway is proposed where the acetate base promotes the rearrangement of the 2,3-epoxycyclohexanone into the active mono-enol form of 1,2-cyclohexanedione. An alternative classically heated procedure for isomerization-C3-arylation of 2,3-epoxycyclohexanone in DMF is also reported.

Photochemical Reactivity of α-Sulfonyloxy Enones: An Easy Method for Arylation of 1,2-Diketones

3-Aryl-1,2-cyclohexanediones 4 are prepared conveniently by photolysis of the corresponding 2-((arylsulfonyl)oxy)cyclohex-2-enones 1.The reaction was shown to occur from a triplet excited state.A biphotonic process involving the normal photo-Fries product 14 as an intermediate was ruled out by preparing and irradiating this compound.The difference of reactivity between 1 and 2-((arylsulfonyl)amido)cyclohexenones is discussed.