Ferrocenyl Substituted Stannanethione and Stannaneselone
Heavier element analogues of a ketone, a C=O double-bond compound, have been fascinating compounds from the viewpoint of main-group element chemistry because of their unique structural features and reactivity as compared with those of a ketone, which plays an important role in organic chemistry. We...
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MDPI AG
2025-06-01
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| author | Keisuke Iijima Koh Sugamata Takahiro Sasamori |
| author_facet | Keisuke Iijima Koh Sugamata Takahiro Sasamori |
| author_sort | Keisuke Iijima |
| collection | DOAJ |
| description | Heavier element analogues of a ketone, a C=O double-bond compound, have been fascinating compounds from the viewpoint of main-group element chemistry because of their unique structural features and reactivity as compared with those of a ketone, which plays an important role in organic chemistry. We will report here the synthesis of diorgano-stannanethione and stannaneselone featuring tin–chalcogen double bonds, which are the heavy-element analogues of a ketone. The newly obtained stannaneselone has been structurally characterized by spectroscopic analyses and single-crystal X-ray diffraction (SC-XRD) analysis, showing the short Sn–Se bond length featuring π-bond character. The obtained bis(ferrocenyl)stannanechalcogenones were found to undergo [2+4]cycloaddition reactions with 2,3-dimethyl-1,3-butadiene, affording the corresponding six-membered ring compound. Notably, thermolysis of the [2+4]cycloadduct of the stannaneselone regenerated the stannaneselone via the retro[2+4]cycloaddition, whereas the sulfur analogue was thermally very stable. |
| format | Article |
| id | doaj-art-d115438900a649e29b8da1f90bca424b |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-d115438900a649e29b8da1f90bca424b2025-08-20T03:49:55ZengMDPI AGMolecules1420-30492025-06-013013282610.3390/molecules30132826Ferrocenyl Substituted Stannanethione and StannaneseloneKeisuke Iijima0Koh Sugamata1Takahiro Sasamori2Graduate School of Science and Technology, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba 305-8571, Ibaraki, JapanDepartment of Chemistry, Institute of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba 305-8571, Ibaraki, JapanDepartment of Chemistry, Institute of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba 305-8571, Ibaraki, JapanHeavier element analogues of a ketone, a C=O double-bond compound, have been fascinating compounds from the viewpoint of main-group element chemistry because of their unique structural features and reactivity as compared with those of a ketone, which plays an important role in organic chemistry. We will report here the synthesis of diorgano-stannanethione and stannaneselone featuring tin–chalcogen double bonds, which are the heavy-element analogues of a ketone. The newly obtained stannaneselone has been structurally characterized by spectroscopic analyses and single-crystal X-ray diffraction (SC-XRD) analysis, showing the short Sn–Se bond length featuring π-bond character. The obtained bis(ferrocenyl)stannanechalcogenones were found to undergo [2+4]cycloaddition reactions with 2,3-dimethyl-1,3-butadiene, affording the corresponding six-membered ring compound. Notably, thermolysis of the [2+4]cycloadduct of the stannaneselone regenerated the stannaneselone via the retro[2+4]cycloaddition, whereas the sulfur analogue was thermally very stable.https://www.mdpi.com/1420-3049/30/13/2826stannanethionestannaneseloneferrocenyl groupcycloadditionstannylene |
| spellingShingle | Keisuke Iijima Koh Sugamata Takahiro Sasamori Ferrocenyl Substituted Stannanethione and Stannaneselone Molecules stannanethione stannaneselone ferrocenyl group cycloaddition stannylene |
| title | Ferrocenyl Substituted Stannanethione and Stannaneselone |
| title_full | Ferrocenyl Substituted Stannanethione and Stannaneselone |
| title_fullStr | Ferrocenyl Substituted Stannanethione and Stannaneselone |
| title_full_unstemmed | Ferrocenyl Substituted Stannanethione and Stannaneselone |
| title_short | Ferrocenyl Substituted Stannanethione and Stannaneselone |
| title_sort | ferrocenyl substituted stannanethione and stannaneselone |
| topic | stannanethione stannaneselone ferrocenyl group cycloaddition stannylene |
| url | https://www.mdpi.com/1420-3049/30/13/2826 |
| work_keys_str_mv | AT keisukeiijima ferrocenylsubstitutedstannanethioneandstannaneselone AT kohsugamata ferrocenylsubstitutedstannanethioneandstannaneselone AT takahirosasamori ferrocenylsubstitutedstannanethioneandstannaneselone |