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- Publisher Website: 10.1021/acs.orglett.3c00042
- Scopus: eid_2-s2.0-85149512622
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Article: Formation of 3-Oxa- and 3-Thiacyclohexyne from Ring Expansion of Heterocyclic Alkylidene Carbenes: A Mechanistic Study
| Title | Formation of 3-Oxa- and 3-Thiacyclohexyne from Ring Expansion of Heterocyclic Alkylidene Carbenes: A Mechanistic Study |
|---|---|
| Authors | |
| Issue Date | 10-Mar-2023 |
| Publisher | American Chemical Society |
| Citation | Organic Letters, 2023, v. 25, n. 9, p. 1364-1369 How to Cite? |
| Abstract | The rearrangement pathways of two alkylidene carbenes appended to an oxa or thiacyclopentane into the corresponding heterocyclohexynes were elucidated using 13C-labeling experiments. Both carbenes exhibited a preference for migration of the allylic carbon bound to the heteroatom. Anomeric interactions involving a heteroatom lone pair and antibonding orbital of the migrating bond and inductive destabilization of the minor migratory pathway are discussed as plausible reasons for the observed trends. |
| Persistent Identifier | http://hdl.handle.net/10722/331325 |
| ISSN | 2023 Impact Factor: 4.9 2023 SCImago Journal Rankings: 1.245 |
| ISI Accession Number ID |
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.author | Anderson, TE | - |
| dc.contributor.author | Thamattoor, DM | - |
| dc.contributor.author | Phillips, DL | - |
| dc.date.accessioned | 2023-09-21T06:54:44Z | - |
| dc.date.available | 2023-09-21T06:54:44Z | - |
| dc.date.issued | 2023-03-10 | - |
| dc.identifier.citation | Organic Letters, 2023, v. 25, n. 9, p. 1364-1369 | - |
| dc.identifier.issn | 1523-7060 | - |
| dc.identifier.uri | http://hdl.handle.net/10722/331325 | - |
| dc.description.abstract | <p></p><p>The rearrangement pathways of two alkylidene carbenes appended to an oxa or thiacyclopentane into the corresponding heterocyclohexynes were elucidated using 13C-labeling experiments. Both carbenes exhibited a preference for migration of the allylic carbon bound to the heteroatom. Anomeric interactions involving a heteroatom lone pair and antibonding orbital of the migrating bond and inductive destabilization of the minor migratory pathway are discussed as plausible reasons for the observed trends.<br></p> | - |
| dc.language | eng | - |
| dc.publisher | American Chemical Society | - |
| dc.relation.ispartof | Organic Letters | - |
| dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
| dc.title | Formation of 3-Oxa- and 3-Thiacyclohexyne from Ring Expansion of Heterocyclic Alkylidene Carbenes: A Mechanistic Study | - |
| dc.type | Article | - |
| dc.identifier.doi | 10.1021/acs.orglett.3c00042 | - |
| dc.identifier.scopus | eid_2-s2.0-85149512622 | - |
| dc.identifier.volume | 25 | - |
| dc.identifier.issue | 9 | - |
| dc.identifier.spage | 1364 | - |
| dc.identifier.epage | 1369 | - |
| dc.identifier.eissn | 1523-7052 | - |
| dc.identifier.isi | WOS:000942878100001 | - |
| dc.identifier.issnl | 1523-7052 | - |