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- W3200859025 endingPage "108033" @default.
- W3200859025 startingPage "108033" @default.
- W3200859025 abstract "The molecular mechanism of the double (3 + 2) cycloaddition (32CA) reaction between nitrile oxides and allenoates has been studied using density functional theory at the M06-2X/6-311G (d,p) level of theory. In the first 32CA, the nitrile oxide adds chemo- and regio-selectively to the C-C double bond of the allenoate closest to the carboxylate group followed by a subsequent regioselective addition to the olefinic bond of the isoxazoline intermediate. The rate constant for the preferred pathway (formation of 4-methylene-2-isoxazoline intermediate) in the reaction of ethyl substituted allenoate and mesitonitrile oxide is 5.3 × 102 s-1 in THF which is about 13 times faster than the closest competing step (formation of its regioisomer 5-methylene-2-isoxazoline intermediate) which has a rate constant of 4.4 × 101 s-1. Strong electron-donating groups (EDGs) and electron-withdrawing groups (EWGs) decrease activation barriers and hence increase the reaction rate. Also, the dimerization of nitrile oxide to form furaxon is found to be kinetically unfavored." @default.
- W3200859025 created "2021-09-27" @default.
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- W3200859025 date "2021-12-01" @default.
- W3200859025 modified "2023-09-27" @default.
- W3200859025 title "A DFT study of the double (3 + 2) cycloaddition of nitrile oxides and allenoates for the formation of spirobiisoxazolines" @default.
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- W3200859025 doi "https://doi.org/10.1016/j.jmgm.2021.108033" @default.
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