Journal
ORGANIC LETTERS
Volume 23, Issue 9, Pages 3751-3754Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01164
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Funding
- NIH [GM101421, AI148740]
- NSF [CHE-1764328]
- Austrian Science Fund (FWF) [J 4216-N28]
- City of Vienna [H331849/2018]
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This study found that in the reactions of oxanorbornadienes, substituents at the 2- and 5-positions have a significant influence on the rate of retro-Diels-Alder reaction, and the fragmentation rate is inversely correlated with electron-withdrawing ability. Density functional theory calculations demonstrated a good correlation with experimentally measured OND rDA rates.
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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