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Mendeley readers
| Title |
AlCl3‑Catalyzed Ring Expansion Cascades of Bicyclic Cyclobutenamides Involving Highly Strained Cis,Trans-Cycloheptadienone Intermediates
|
|---|---|
| Published in |
Journal of the American Chemical Society, April 2015
|
| DOI | 10.1021/jacs.5b02561 |
| Pubmed ID | |
| Authors |
Xiao-Na Wang, Elizabeth H. Krenske, Ryne C. Johnston, K. N. Houk, Richard P. Hsung |
| Abstract |
We report the first experimental evidence for the generation of highly strained cis,trans-cycloheptadienones by electrocyclic ring opening of 4,5-fused cyclobutenamides. In the presence of AlCl3, the cyclobutenamides rearrange to [2.2.1]-bicyclic ketones; DFT calculations provide evidence for a mechanism involving torquoselective 4π-electrocyclic ring opening to a cis,trans-cycloheptadienone followed by a Nazarov-like recyclization and a 1,2-alkyl shift. Similarly, 4,6-fused cyclobutenamides undergo AlCl3-catalyzed rearrangements to [3.2.1]-bicyclic ketones through cis,trans-cyclooctadienone intermediates. The products can be further elaborated via facile cascade reactions to give complex tri- and tetracyclic molecules. |
Mendeley readers
The data shown below were compiled from readership statistics for 27 Mendeley readers of this research output. Click here to see the associated Mendeley record.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 27 | 100% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 6 | 22% |
| Researcher | 6 | 22% |
| Student > Master | 4 | 15% |
| Student > Bachelor | 3 | 11% |
| Professor | 2 | 7% |
| Other | 3 | 11% |
| Unknown | 3 | 11% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 22 | 81% |
| Materials Science | 1 | 4% |
| Physics and Astronomy | 1 | 4% |
| Unknown | 3 | 11% |