Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye
Metodej Dvoracek, Brendan Twamley, Mathias O Senge, Mikhail A Filatov
TL;DR
Researchers used visible light to trigger a chemical reaction in a modified bimane dye, enabling the creation of cyclobutane compounds without UV light.
Contribution
The study introduces a visible light-initiated topochemical [2 + 2] cycloaddition in functionalized bimane dyes.
Findings
Visible light initiates topochemical [2 + 2] cycloaddition in Cl2B.
Functionalizing bimanes redshifts absorption into the visible spectrum.
Crystal structure confirms parallel and coplanar reactive double bonds.
Abstract
Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation.
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Taxonomy
TopicsRadical Photochemical Reactions · Photochromic and Fluorescence Chemistry · Axial and Atropisomeric Chirality Synthesis