One-Pot Access to Push–Pull Oligoenes by Sequential [2 + 2] Cycloaddition–Retroelectrocyclization Reactions

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• 作者：Govindasamy Jayamurugan ; Aaron D. Finke ; Jean-Paul Gisselbrecht ; Corinne Boudon ; W. Bernd Schweizer ; Fran?ois Diederich
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：January 3, 2014
• 年：2014
• 卷：79
• 期：1
• 页码：426-431
• 全文大小：333K
• ISSN：1520-6904

文摘

The formal [2 + 2] cycloaddition鈥搑etroelectrocyclization reaction was employed as the key transformation to obtain donor-substituted, 蟺-conjugated polycyanohexa-1,3,5-trienes (TCHTs and PCHTs) and polycyanoocta-1,3,5,7-tetraenes from donor-substituted tetracyanobuta-1,3-dienes (TCBDs) and electron-rich alkynes. These push鈥損ull-substituted oligoene chromophores were also accessed in good yield from tetracyanoethylene and donor-substituted alkynes by using a one-pot protocol. All bis-(N,N-dialkylanilino) donor-substituted push鈥損ull trienes and tetraenes showed better electron-accepting potency and lower HOMO鈥揕UMO gaps than the corresponding TCBDs, as evidenced by optical and electrochemical studies.