Baroudi, Abdulkader

Karton, Amir

2021-09

<p>A mechanism for the thermal instability and selective rearrangement of 2-bromooxazolines is proposed and examined using the highly accurate G4(MP2) thermochemical protocol. We propose this rearrangement to be autocatalyzed by bromide ions that are initially formed via a bimolecular reaction between two 2-bromooxazoline molecules. We find this step to be rate determining, and it results in a consequent and more favorable propagative reaction of bromide ions with the starting material (2-bromooxazoline). The proposed mechanism sheds light on experimental observations and provides a coherent explanation for 2-bromooxazolines thermal instability. We proceed to rationalize the high barrier of the rate-determining step via comparison with experimentally known pathways.</p>

Journal of Physical Organic Chemistry, 34(9), p. 1-6

1099-1395

0894-3230

https://hdl.handle.net/1959.11/47324

John Wiley & Sons Ltd

Mechanistic insights into the autocatalyzed rearrangement of 2‐bromooxazolines to 2‐bromoisocyanates by means of high‐level quantum chemical methods

Journal Article

Publication