Treatment of epoxides with bis(trimethylsilyl)-selenide under strictly controlled conditions allows to isolate b-hydroxy selenols which evidence an unexpected stability, taking into account their known propensity to afford diselenides. Also thiiranes and aziridines lead to functionalized selenols bearing a thiol and a N-Ts- or N-Boc-protected amino moiety on b-position. These selenols were stable enough to react with different electrophiles. Ab-initio DF calculations on two suitable model systems, n-propyl selenol and bhydroxy derivative, allow to ascribe the observed low tendency to oxidation to noncovalent interactions between the selenol moiety and theOH group.

A Straightforward Access to Stable β-Functionalized Alkyl Selenols / Damiano Tanini,Caterina Tiberi, Cristina Gellini, Pier Remigio Salvi, Antonella Capperucci. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4169. - ELETTRONICO. - 360:(2018), pp. 3367-3375. [10.1002/adsc.201800602]

A Straightforward Access to Stable β-Functionalized Alkyl Selenols

Damiano Tanini
Membro del Collaboration Group
;
Caterina Tiberi;Cristina Gellini;Pier Remigio Salvi;Antonella Capperucci
2018

Abstract

Treatment of epoxides with bis(trimethylsilyl)-selenide under strictly controlled conditions allows to isolate b-hydroxy selenols which evidence an unexpected stability, taking into account their known propensity to afford diselenides. Also thiiranes and aziridines lead to functionalized selenols bearing a thiol and a N-Ts- or N-Boc-protected amino moiety on b-position. These selenols were stable enough to react with different electrophiles. Ab-initio DF calculations on two suitable model systems, n-propyl selenol and bhydroxy derivative, allow to ascribe the observed low tendency to oxidation to noncovalent interactions between the selenol moiety and theOH group.
2018
360
3367
3375
Damiano Tanini,Caterina Tiberi, Cristina Gellini, Pier Remigio Salvi, Antonella Capperucci
File in questo prodotto:
File Dimensione Formato  
adsc.201800602.pdf

Accesso chiuso

Tipologia: Versione finale referata (Postprint, Accepted manuscript)
Licenza: Tutti i diritti riservati
Dimensione 2.23 MB
Formato Adobe PDF
2.23 MB Adobe PDF   Richiedi una copia

I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1130947
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 43
  • ???jsp.display-item.citation.isi??? 43
social impact