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Frontier-Controlled Pericyclic Reactions of Powerful Electron-Attracting Cyclic Dienones and Diazadienones with 1H-Azepine: Molecular Structures of Cycloadducts and Some Comments
Harano, Kazunobu,Yasuda, Masami,Ban, Takashi,Kanematsu, Ken
, p. 4455 - 4462 (2007/10/02)
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.
