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Photoisomerization as a trigger for Bergman cyclization: synthesis and reactivity of azoenediynes. | LitMetric

Cyclic enediynes 1a and 2a containing stable E-azo moiety (azoenediynes) have been synthesized. These compounds upon irradiation with long wavelength UV isomerize to the Z-compounds 1b and 2b, which can be thermally reisomerized to the Z compounds. Reactivity studies toward BC using DSC predictably indicate higher reactivity for the Z-isomers. Our studies may provide a novel way to modulate the reactivity of enediynes under thermal or photochemical conditions.

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http://dx.doi.org/10.1016/j.bmcl.2005.09.005DOI Listing

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