| Title: |
Gold-Catalyzed Rearrangement of Propargyl Alcohols Using Coupling Constants to Determine Isomeric Ratios |
| Language: |
English |
| Authors: |
Cheng, Xinpeng; Chen, Jonna; Gainer, Morgan J. (ORCID 0000-0002-4034-687X); Zhang, Liming (ORCID 0000-0002-5306-1515) |
| Source: |
Journal of Chemical Education. Oct 2019 96(10):2348-2351. |
| Availability: |
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc |
| Peer Reviewed: |
Y |
| Page Count: |
4 |
| Publication Date: |
2019 |
| Document Type: |
Journal Articles; Reports - Descriptive |
| Education Level: |
Higher Education; Postsecondary Education |
| Descriptors: |
Organic Chemistry; Synthesis; College Science; Science Instruction; Science Experiments; Metallurgy; Spectroscopy |
| DOI: |
10.1021/acs.jchemed.9b00007 |
| ISSN: |
0021-9584 |
| Abstract: |
Gold is an increasingly prominent transition metal in organic synthesis. The air-stable, water-insensitive cationic gold(I) catalysts enable varieties of synthetic transformations with a simple reaction setup. However, this increased importance has not coincided with an increase in the application of gold in second-year organic chemistry courses. An experiment is described that includes a gold-catalyzed rearrangement of propargyl alcohols targeted at second-year organic chemistry students. The reaction produces a mixture of "E" and "Z" isomers of an enone product that students analyze by [superscript 1]H NMR spectroscopy to determine the major product. |
| Abstractor: |
As Provided |
| Entry Date: |
2019 |
| Accession Number: |
EJ1231343 |
| Database: |
ERIC |