Zeitschriftenartikel:
L. De Pascalis, M. Yau, D. Svatunek, Z. Tan, S. Tekkam, K. Houk, M. Finn:
"The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation";
Organic Letters,
23
(2021),
9;
4 S.
Kurzfassung englisch:
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.
Schlagworte:
Cycloaddition Reaction; Electrons; Furans; Molecular Structure; Sulfhydryl Compounds
"Offizielle" elektronische Version der Publikation (entsprechend ihrem Digital Object Identifier - DOI)
http://dx.doi.org/10.1021/acs.orglett.1c01164
Elektronische Version der Publikation:
https://publik.tuwien.ac.at/files/publik_303202.pdf
Erstellt aus der Publikationsdatenbank der Technischen Universität Wien.