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翻訳と辞書　辞書検索 [ 開発暫定版 ] スポンサード リンク Cope rearrangement ： ウィキペディア英語版 Cope rearrangement The Cope rearrangement is an extensively studied organic reaction involving the ()-sigmatropic rearrangement of 1,5-dienes.〔Arthur C. Cope; ''et al.''; ''J. Am. Chem. Soc.'' 1940, ''62'', 441.〕〔Rhoads, S. J.; Raulins, N. R.; ''Org. React.'' 1975, ''22'', 1–252. (Review)〕〔Hill, R. K.; ''Comp. Org. Syn.'' 1991, ''5'', 785–826.〕〔Wilson, S. R.; ''Org. React.'' 1993, ''43'', 93–250. (Review)〕 It was developed by Arthur C. Cope. For example 3-methyl-1,5-hexadiene heated to 300°C yields 1,5-heptadiene. The Cope rearrangement causes the fluxional states of the molecules in the bullvalene family. ==Mechanism== Although the Cope rearrangement is concerted and pericyclic, it can also be considered to go via a transition state that is energetically and structurally equivalent to a diradical.〔Michael B. Smith & Jerry March: March's Advanced Organic Chemistry, pp. 1659-1673. John Wiley & Sons, 2007. ISBN 978-0-471-72091-1.〕 This is an alternative explanation which remains faithful to the uncharged nature of the Cope transition state, while preserving the principles of orbital symmetry. This also explains the high energy requirement to perform a Cope rearrangement. Although illustrated in the chair conformation, the Cope can also occur with cyclohexadienes in the "boat" conformation. The above description of the transition state is not quite correct. It is currently generally accepted that the Cope rearrangement follows an allowed concerted route through a homoaromatic transition state and not a diradical. That is unless the potential energy surface is perturbed to favor the diradical.〔Williams, R. V., Chem. Rev. 2001, 101 (5), 1185–1204.〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Cope rearrangement」の詳細全文を読む スポンサード リンク 翻訳と辞書 : 翻訳のためのインターネットリソース Copyright(C) kotoba.ne.jp 1997-2016. All Rights Reserved.