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Jayamurugan G, Finke AD, Gisselbrecht JP, et al. One-pot access to push-pull oligoenes by sequential [2 + 2] cycloaddition-retroelectrocyclization reactions. J Org Chem. 2013;79(1):426-31doi: 10.1021/jo402440m.
Jayamurugan, G., Finke, A. D., Gisselbrecht, J. P., Boudon, C., Schweizer, W. B., & Diederich, F. (2014). One-pot access to push-pull oligoenes by sequential [2 + 2] cycloaddition-retroelectrocyclization reactions. The Journal of organic chemistry, 79(1), 426-31. https://doi.org/10.1021/jo402440m
Jayamurugan, Govindasamy, et al. "One-pot access to push-pull oligoenes by sequential [2 + 2] cycloaddition-retroelectrocyclization reactions." The Journal of organic chemistry vol. 79,1 (2014): 426-31. doi: https://doi.org/10.1021/jo402440m
Jayamurugan G, Finke AD, Gisselbrecht JP, Boudon C, Schweizer WB, Diederich F. One-pot access to push-pull oligoenes by sequential [2 + 2] cycloaddition-retroelectrocyclization reactions. J Org Chem. 2014 Jan 03;79(1):426-31. doi: 10.1021/jo402440m. Epub 2013 Dec 11. PMID: 24328401.
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J Org Chem. 2014 Jan 03;79(1):426-31. doi: 10.1021/jo402440m. Epub 2013 Dec 11.

One-pot access to push-pull oligoenes by sequential [2 + 2] cycloaddition-retroelectrocyclization reactions.

The Journal of organic chemistry

Govindasamy Jayamurugan, Aaron D Finke, Jean-Paul Gisselbrecht, Corinne Boudon, W Bernd Schweizer, François Diederich

Affiliations

  1. Laboratorium für Organische Chemie, ETH-Zürich , Hönggerberg, HCI, CH-8093 Zürich, Switzerland.

PMID: 24328401 DOI: 10.1021/jo402440m

Abstract

The formal [2 + 2] cycloaddition-retroelectrocyclization reaction was employed as the key transformation to obtain donor-substituted, π-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-pull-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-pull trienes and tetraenes showed better electron-accepting potency and lower HOMO-LUMO gaps than the corresponding TCBDs, as evidenced by optical and electrochemical studies.

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