| Author(s) |
Baroudi, Abdulkader
Karton, Amir
|
| Publication Date |
2021-09
|
| Abstract |
<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>
|
| Citation |
Journal of Physical Organic Chemistry, 34(9), p. 1-6
|
| ISSN |
1099-1395
0894-3230
|
| Link | |
| Language |
en
|
| Publisher |
John Wiley & Sons Ltd
|
| Title |
Mechanistic insights into the autocatalyzed rearrangement of 2‐bromooxazolines to 2‐bromoisocyanates by means of high‐level quantum chemical methods
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| Type of document |
Journal Article
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| Entity Type |
Publication
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