Aminium Hexachloroantimonate Salts as Latent Sources of Antimony Pentachloride in Pinacolic Rearrangement of Vicinal Diols

Aminium Hexachloroantimonate Salts as Latent Sources of Antimony Pentachloride in Pinacolic Rearrangement of Vicinal Diols

Rearrangements of various vicinal diols (1a–f) induced by hexachloroantimonate aminium salts A or B were found to occur in a similar manner when antimony pentachloride was used instead of aminium salts. Antimony pentachloride is proposed as the active catalytic species, possibly deriving from the ox...

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Veröffentlicht in:European Journal of Organic Chemistry 2005-04, Vol.2005 (8), p.1597-1603
Hauptverfasser: Ciminale, Luigi Lopez, Francesco, Nacci, Angelo, D'Accolti, Lucia, Vitale, Floriana
Format: Artikel
Sprache:eng
Schlagworte:
Aminium salts
Antimony pentachloride
Lewis acid
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Zusammenfassung:Rearrangements of various vicinal diols (1a–f) induced by hexachloroantimonate aminium salts A or B were found to occur in a similar manner when antimony pentachloride was used instead of aminium salts. Antimony pentachloride is proposed as the active catalytic species, possibly deriving from the oxidation of the hexachloroantimonate anion SbCl6– by the aminium counterpart. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400701