Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene
1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C6H4(CHO)2 undergo cascades to tetracenes on simple admixture of LiHDMS, CS2 and MeI. Acene formation proceeds by [3,3]-sigmatropic rearrangement of xanthate anions followed by 6π electrocyclisat...
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Beilstein-Institut
2015
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| Online Access: | https://eprints.nottingham.ac.uk/46641/ |
| _version_ | 1848797375176376320 |
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| author | Burroughs, Laurence Ritchie, John Ngwenya, Mkhethwa Khan, Dilfaraz Lewis, William Woodward, Simon |
| author_facet | Burroughs, Laurence Ritchie, John Ngwenya, Mkhethwa Khan, Dilfaraz Lewis, William Woodward, Simon |
| author_sort | Burroughs, Laurence |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C6H4(CHO)2 undergo cascades to tetracenes on simple admixture of LiHDMS, CS2 and MeI. Acene formation proceeds by [3,3]-sigmatropic rearrangement of xanthate anions followed by 6π electrocyclisations. The reactions are terminated by E2 or anionic Chugaev-type eliminations. Structural packing motifs and electronic properties are reported for the tetracenes. |
| first_indexed | 2025-11-14T20:02:52Z |
| format | Article |
| id | nottingham-46641 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:02:52Z |
| publishDate | 2015 |
| publisher | Beilstein-Institut |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-466412020-05-04T17:02:17Z https://eprints.nottingham.ac.uk/46641/ Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene Burroughs, Laurence Ritchie, John Ngwenya, Mkhethwa Khan, Dilfaraz Lewis, William Woodward, Simon 1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph, substituted phenyl, 2-thienyl) to ortho-C6H4(CHO)2 undergo cascades to tetracenes on simple admixture of LiHDMS, CS2 and MeI. Acene formation proceeds by [3,3]-sigmatropic rearrangement of xanthate anions followed by 6π electrocyclisations. The reactions are terminated by E2 or anionic Chugaev-type eliminations. Structural packing motifs and electronic properties are reported for the tetracenes. Beilstein-Institut 2015-02-20 Article PeerReviewed Burroughs, Laurence, Ritchie, John, Ngwenya, Mkhethwa, Khan, Dilfaraz, Lewis, William and Woodward, Simon (2015) Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene. Beilstein Journal of Organic Chemistry, 11 . pp. 273-279. ISSN 1860-5397 allenes; anionic Chugaev rearrangement; anionic sigmatropic rearrangement; tetracene properties; X-ray structures http://www.beilstein-journals.org/bjoc/articles/11/31 doi:10.3762/bjoc.11.31 doi:10.3762/bjoc.11.31 |
| spellingShingle | allenes; anionic Chugaev rearrangement; anionic sigmatropic rearrangement; tetracene properties; X-ray structures Burroughs, Laurence Ritchie, John Ngwenya, Mkhethwa Khan, Dilfaraz Lewis, William Woodward, Simon Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene |
| title | Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene |
| title_full | Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene |
| title_fullStr | Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene |
| title_full_unstemmed | Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene |
| title_short | Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene |
| title_sort | anionic sigmatropic-electrocyclic-chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene |
| topic | allenes; anionic Chugaev rearrangement; anionic sigmatropic rearrangement; tetracene properties; X-ray structures |
| url | https://eprints.nottingham.ac.uk/46641/ https://eprints.nottingham.ac.uk/46641/ https://eprints.nottingham.ac.uk/46641/ |