Publications [#368040] of Stephen L Craig

Journal Articles

1. Wang, L; Zheng, X; Kouznetsova, TB; Yen, T; Ouchi, T; Brown, CL; Craig, SL, Mechanochemistry of Cubane., Journal of the American Chemical Society, vol. 144 no. 50 (December, 2022), pp. 22865-22869 [doi]
   (last updated on 2026/01/17)

   Abstract:
   We report the mechanochemical reactivity of the highly strained pentacyclic hydrocarbon cubane. The mechanical reactivity of cubane is explored for three regioisomers with 1,2-, 1,3-, and 1,4-substituted pulling attachments. Whereas all compounds can be activated thermally, mechanical activation is observed via pulsed ultrasonication of cubane-containing polymers only when force is applied via 1,2-attachment. The single observed product of the force-coupled reaction is a thermally inaccessible syn-tricyclooctadiene, in contrast to cyclooctatetraene (observed thermally) or a pair of cyclobutadienes that would result from sequential cyclobutane scission. We further quantify the mechanochemical reactivity of cubane by single molecule force spectroscopy, and force-coupled rate constants for ring opening reach ∼33 s^-1 at a force of ∼1.55 nN, lower than forces of 1.8-2.0 nN that are typical of conventional cyclobutanes.