AI Article Synopsis
- The study investigates the Ritter-type C-H amination reaction of menthol with acetonitrile, originally reported by Baran et al. in 2012, utilizing advanced techniques like mass spectrometry, UV/vis monitoring, and computational calculations.
- It confirms Baran's initial mechanism while revealing an additional pathway for product formation that appears to occur specifically in microdroplets.
- The calculations indicate both pathways operate with low energy barriers, making them feasible under normal atmospheric conditions.
Article Abstract
The mechanism of the Ritter-type C-H amination reaction of menthol with acetonitrile using CuBr, Selectfluor, and Zn(OTf), first disclosed by Baran and coworkers in 2012, was studied using a combination of online electrospray ionization mass spectrometry, continuous UV/vis spectrometric monitoring, and density functional theory calculations. In addition to corroborating Baran's original mechanistic proposal, these studies uncovered a second pathway to product formation, which likely only occurs in microdroplets. DFT calculations show that neither pathway has a barrier that is greater than 6.8 kcal/mol, suggesting that both mechanisms are potentially operative under ambient conditions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.8b00690 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!