| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1322377 | Journal of Organometallic Chemistry | 2014 | 8 Pages |
•Routes to the ferrocene-derived selenols Fc(CH2)nSeH have been explored.•Intermediate selenocyanate FcCH2SeCN has been structurally characterised.•Stabilisation effect of ferrocene in arsines and phosphines not extended to selenols.
Ferrocenyl-methyl and -butyl selenols Fc(CH2)nSeH (n = 1 or 4) have been prepared by reduction of the corresponding selenocyanates Fc(CH2)nSeCN (n = 1 or 4) with NaBH4 or the corresponding diselenide FcCH2SeSeCH2Fc with Zn/HCl or NaBH4. The compounds were characterised by NMR and IR spectroscopy and GCMS and/or ESI MS. The selenols were found to be substantially air-sensitive regardless of the presence of a Fc(CH2)n group at the hydride centre. The X-ray crystal structure of FcCH2SeCN is also reported.
Graphical abstractRoutes to the synthesis of the ferrocenylalkylselenols Fc(CH2)nSeH (n = 1 or 4), via the selenocyanates Fc(CH2)nSeCN or diselenides Fc(CH2)nSeSe(CH2)nFc have been explored; the previously observed stabilisation effect of the ferrocenylalkyl group on phosphines and arsines is not extended to the selenides, which are appreciably air-sensitive.Figure optionsDownload full-size imageDownload as PowerPoint slide
