–i. The IBO method provides a convenient quantitative method for deriving curly arrows in a rational manner rather than the normal ad hoc representations used ubiquitously in teaching organic chemistry. This criterion simplifies the identification of IBOs that are to be inspected in a given transformation. The EUMOσ* is in the same as or even lower level than the HOMO energy of alkenes. Mechanism on epoxidation of alkenes by peracids: A protonation-promoted pathway and its quantum chemical elucidation. One could argue that curly arrows are merely a formalism4, 16 and that they were not intended to capture the intricate changes that the electronic structure undergoes during a reaction. The textbook representations do not take this subtle difference into account and therefore fail to provide even a qualitative description of the underlying changes to the electronic structure. Variation in the substituents on the ethene can be seen to strongly influence whether a proton transfer occurs before or after the C−O bonds are formed. These results are attributed to the H-bond interactions of substrate 1 with the silanol and carboxylic acid groups bonded to … Probably the most commonly used is mCPBA as it is a readily available, easy to handle solid. Alkenes reacts with peroxycarboxylic acid to give oxacyclopropanes (epoxides). It is crucial to appreciate that the major differences are a result of the orientation of bonds and Ione pairs featuring π symmetry and their changes. As the O−O bond scission occurs in a concerted fashion, plot II indicates that the proton transfer occurs only after the epoxide is fully formed. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. If you do not receive an email within 10 minutes, your email address may not be registered, or in a thesis or dissertation provided that the correct acknowledgement is given To augment our studies we also highlight the importance of the changes to the dipole moment during the course of the IRC for these reactions as an indicator of “hidden” ionic intermediates during the course of the reaction.13. In the present case we can see in group I that the two C−O bonds in the epoxide are not formed in a synchronous fashion. Instead, the initial C−O bond is formed upon nucleophilic attack of the alkene onto the electrophilic oxygen, which occurs with an SN2‐like concomitant O−O bond scission. The protonation site is the oxygen atom of carbonyl group in peracids. The changes in dipole moment, as indicators of hidden ionic intermediates at the proton transfer stages, also reflect this (Figure 4). To recover these insights from curly arrow representations of the mechanisms does require inclusion of additional information such as that imparted in Figure 3; conventional curly arrows on their own can be insufficient to represent this information.
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