Homoconjugated and Spiro Push–Pull Systems: Cycloadditions of Naphtho- and Anthradiquinones with Electron-Rich Alkynes
Author(s)Dengiz, Cagatay; Swager, Timothy M
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We report the synthesis and characterization of three new classes of push–pull chromophores using [2+2]-cycloaddition reactions of electron-rich alkynes and electron-poor alkenes. Previous investigations have focused on the reactions of cyano-substituted electron acceptors. This study demonstrates that cyano-free electron acceptors, naphtho- and anthradiquinones, can also be used to access extended push–pull systems. The effects of the structural changes on the spectroscopic and electronic properties were investigated by UV/vis spectroscopy. Structures were confirmed by X-ray and NMR analysis in solution. Keywords: homoconjugation - cycloaddition - push–pull - quinones - spirocycles
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Thieme Publishing Group
Dengiz, Cagatay, and Timothy Swager. “Homoconjugated and Spiro Push–Pull Systems: Cycloadditions of Naphtho- and Anthradiquinones with Electron-Rich Alkynes.” Synlett, vol. 28, no. 12, July 2017, pp. 1427–31.