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Iminium Salts of ω-Dithiafulvenylpolyenals: An Easy Entry to the Corresponding Aldehydes and Doubly Proaromatic Nonlinear Optic-phores

Abstract :

A short, high-yielding route to ω-dithiafulvenylpolyenals (1) via the corresponding iminium salts (2) and starting from trimethyl-1,3-dithiolium tetrafluoroborate is reported. The Knoevenagel reactions of either 1 or 2 with isoxazolone-containing acceptors afford merocyanines 7 and 9, in a process that is often accompanied by a vinylene-shortening side reaction. Experimental and theoretical studies reveal that compounds 7 and 9, featuring two proaromatic end groups, are strongly polarized and show good second-order nonlinear optical responses.

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https://hal.univ-angers.fr/hal-03027814
Contributeur : Okina Université d'Angers <>
Soumis le : vendredi 27 novembre 2020 - 12:28:05
Dernière modification le : samedi 28 novembre 2020 - 03:27:37

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Silvia Alías, Raquel Andreu, María-Jesús Blesa, Miguel-Angel Cerdán, Santiago Franco, et al.. Iminium Salts of ω-Dithiafulvenylpolyenals: An Easy Entry to the Corresponding Aldehydes and Doubly Proaromatic Nonlinear Optic-phores. Journal of Organic Chemistry, American Chemical Society, 2008, 73 (15), pp.5890 - 5898. ⟨10.1021/jo800801q⟩. ⟨hal-03027814⟩

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