72003-84-0

Upstream product

• 16691-79-5 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone 
• 2955-79-5 N-ethoxycarbonylazepine 
• 74947-88-9 (1R,2S,8R,9S)-12-Oxo-10,11-diphenyl-5-aza-tricyclo[7.2.1.0^2,8]dodeca-3,6,10-triene-1,5,9-tricarboxylic acid 5-ethyl ester 1,9-dimethyl ester 

Downstream Products

• 77920-77-5 1,2-diphenyl-5,7-bis(methoxycarbonyl)-11-(ethoxycarbonyl)-11-azapentacyclo<5.5.0.0^2,5.0^3,12.0^4,8>dodeca-9-en-6-one 

Relevant academic research and scientific papers

Pericyclic reactions of cyclopentadienones with nonactivated olefins in phenolic solvents. Enhancement of the reactivity and periselectivity

The solvent effect of phenols on the reactivity and periselectivity for the pericyclic reactions of cyclopentadienones with olefins involving conjugated medium-ring polyenes has been investigated. The use of phenols as a solvent accelerates tile reaction rates of cycloadditions of cyclopentadienones with nonactivated olefins. In the reaction of cycloheptatriene in p-chlorophenol, the exo [4+6]π cycloadduct was produced predominantly, in which a 15-fold increase of the reaction rate was observed as compared with that in benzene. The [3,3]-sigmatropy and decarbonylation of the primary cycloadducts were also accelerated by phenols. The possible role of phenols is discussed on the basis of kinetic and molecular orbital (MO) calculation data.

Frontier-Controlled Pericyclic Reactions of Powerful Electron-Attracting Cyclic Dienones and Diazadienones with 1H-Azepine: Molecular Structures of Cycloadducts and Some Comments

Pericyclic reactions of 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone (1a) and 2,5-diphenyl-3,4-diazacyclopentadienone (1d) with N-(ethoxycarbonyl)azepine (2a) were investigated. For 1a, novel exo? and anti endo ? cycloadducts were obtained, whereas for 1d, only the anti endo ? cycloadduct was obtained. These structures were verified by X-ray crystallography. The anti endo ? cycloadduct was found to be formed via Cope rearrangement of the endo ? cycloadduct by UV spectrometry. Compounds 1 are found to have high reactivities toward 2a, and the selectivities were discussed in terms of frontier molecular orbital theory, indicating that 1 is a useful 4? component with inverse electron demand.