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Sudden Isomerization of Oxetane-Carboxylic Acids – substrate design.


Sudden Isomerization of Oxetane-Carboxylic Acids – substrate design.

Having established a viable mannequin for the sudden isomerism of oxetane carboxylic acids to lactones[1], and brought a have a look at a variation within the proton switch catalyst wanted to perform the transformation, I now examine the substrate itself.

R’ is ready to have three values, R’=H (the unique substituent), R’= CH3 and R’= CF3 (FAIR information DOI: 10.14469/hpc/10820)

R’ ΔG, kcal/mol
H 27.0
CH3 29.1
CF3 39.6

The inference is clear-cut; to inhibit the isomerisation to a lactone, CF3 teams substituted onto the methylene teams of the oxetane will successfully do that, with CH3 itself having a a lot weaker impact.


DOI: 10.14469/hpc/10861 and 10.14469/hpc/10862


References


  1. B. Chalyk, A. Grynyova, Ok. Filimonova, T.V. Rudenko, D. Dibchak, and P.Ok. Mykhailiuk, “Sudden Isomerization of Oxetane-Carboxylic Acids”, Natural Letters, vol. 24, pp. 4722-4728, 2022. http://dx.doi.org/10.1021/acs.orglett.2c01402

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