Organic Chemistry

An E-Z route to photobases

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Science  28 Aug 2015:
Vol. 349, Issue 6251, pp. 940-941
DOI: 10.1126/science.349.6251.940-c

Although many stable photoactivated acids are known, there are fewer examples of photoactivated Lewis bases, most of which form by the liberation of protecting or blocking groups. He et al. report that a molecule with a conjugated nitrogen framework, a triazabutadiene, becomes more basic in water (by almost one pH unit) when the absorption of ultraviolet light rotates a double bond and converts the E isomer to the Z form. An organic-soluble derivative was used to catalyze a condensation reaction, the Henry reaction between nitroethane and p-nitrobenzaldehyde.

J. Am. Chem. Soc. 10.1021/jacs.5b04367 (2015).

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