The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms Journal Article
| Authors: | Jones, G. O.; Li, X.; Hayden, A. E.; Houk, K. N.; Danishefsky, S. J. |
| Article Title: | The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms |
| Abstract: | (Chemical Equation Presented) Mechanisms for the recently described reactions of isonitriles with carboxylic acids (Li, X.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 5446) are explored with the B3LYP density functional method. The mechanism involves the formation of a carboxylate mixed formimidic anhydride intermediate via a concerted mechanism. This intermediate is then transformed to an N-formylamide by a concerted pseudopericyclic [1,3]-acyl shift. Mechanisms involving zwitterions or diradicals are discounted. © 2008 American Chemical Society. |
| Keywords: | chemistry; nitriles; nitrile; carboxylic acids; carboxylic acid; quantum theory; acid anhydride; anhydrides |
| Journal Title: | Organic Letters |
| Volume: | 10 |
| Issue: | 18 |
| ISSN: | 1523-7060 |
| Publisher: | American Chemical Society |
| Date Published: | 2008-01-01 |
| Start Page: | 4093 |
| End Page: | 4096 |
| Language: | English |
| DOI: | 10.1021/ol8016287 |
| PUBMED: | 18707109 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 25" - "Export Date: 17 November 2011" - "Source: Scopus" |
