De Pascalis, L., Yau, M.-K., Svatunek, D., Tan, Z., Tekkam, S., Houk, K. N., & Finn, M. G. (2021). The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation. Organic Letters, 23(9), 3751–3754. https://doi.org/10.1021/acs.orglett.1c01164
Oxanorbornadienes (ONDs) undergo facile Michael addition with thiols and then fragment by a retro-Diels-Alder (rDA) reaction, a unique two-step sequence among electrophilic cleavable linkages. The rDA reaction rate was explored as a function of the furan structure, with substituents at the 2- and 5-positions found to be the most influential and the fragmentation rate to be inversely correlated with electron-withdrawing ability. Density functional theory calculations provided an excellent correlation with the experimentally measured OND rDA rates.
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außerhalb der gesamtuniversitären Forschungsschwerpunkte: 50% Computational Materials Science: 50%
