Das, Joyee ; Bag, Subhendu Sekhar ; Basak, Amit (2016) Mechanistic Studies on Garratt–Braverman Cyclization: The Diradical–Cycloaddition Puzzle Journal of Organic Chemistry, 81 (11). pp. 4623-4632. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/Acs.Joc.6B00490
Related URL: http://dx.doi.org/10.1021/Acs.Joc.6B00490
Abstract
In this work, we present the results of extensive multiprong studies involving the fate of deuterium-labeled substrates, EPR, trapping experiments, and LA-LDI mass spectrometry to sort out the controversies relating to the mechanism of Garratt-Braverman cyclization in two systems, namely bis-propargyl sulfones and ethers. The results are in conformity with a diradical mechamism for the sulfone, while for the ether, the anionic [4 + 2] appears to be the preferred pathway. This shows that the mechanistic pathway toward GB cyclization is dependent upon the nature of heteroatom (O or S in sulfone) bridging the propargyl arms.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 130043 |
| Deposited On: | 05 Dec 2022 05:45 |
| Last Modified: | 05 Dec 2022 05:45 |
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