Investigations into the synthesis of ferrocenylalkyl-selenols

• 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.

Routes 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 as PowerPoint slide