Insights into
the Diels–Alder Reaction of Furan
with Maleic Anhydride from Its Prereactive Intermediate
Posted on 2023-01-12 - 16:03
The prereactive intermediate in the furan-maleic anhydride
cycloaddition,
a classical Diels–Alder reaction, has been captured and characterized
in pulsed jets by Fourier transform microwave spectroscopy for the
first time. The observed species is stabilized by the π–π*
interaction between the two moieties, which connects to the endo channel of the cycloaddition. The secondary interactions
between the C=C and C=O in the observed isomer are accountable for
its lower energy with respect to the one with the exo channel. The present study tries to fill the significant void of
the experimental information on prereactive intermediates as the first
stage of Diels–Alder cycloadditions, by outlining the stability
of the prereactive intermediate and its accurate molecular structure
and by emphasizing the role of the π–π* interaction
in governing the stereochemical outcome of the reaction.
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Zhang, Xinyue; Tian, Xiao; Li, Jiayi; Li, Meng; Gao, Tianyue; Zou, Siyu; et al. (2023). Insights into
the Diels–Alder Reaction of Furan
with Maleic Anhydride from Its Prereactive Intermediate. ACS Publications. Collection. https://doi.org/10.1021/acs.jpclett.2c03560
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AUTHORS (10)
- XZXinyue ZhangXTXiao TianJLJiayi LiMLMeng LiTGTianyue GaoSZSiyu ZouJCJunhua ChenXXXuefang XuQGQian GouJGJens-Uwe Grabow
KEYWORDS
π – πpresent study triesaccurate molecular structuremaleic anhydride cycloadditionmaleic anhydridetwo moietiesstereochemical outcomesignificant voidsecondary interactionspulsed jetsprereactive intermediatesprereactive intermediateobserved speciesobserved isomerlower energyfirst timefirst stageexperimental informationexo endo