Acyl-isothiocyanates as Efficient Thiocyanate Transfer Reagents

Acyl-isothiocyanates as Efficient Thiocyanate Transfer Reagents

An unprecedented transfer of a thiocyanate (−SCN) group from aroyl/acyl isothiocyanate to alkyl or benzylic bromide is observed in the presence of a tertiary amine. This process is most effective when the bromomethyl proton is less acidic, while the presence of a more acidic proton gives 1,3-oxathio...

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Veröffentlicht in:Organic letters 2009-08, Vol.11 (15), p.3382-3385
Hauptverfasser: Palsuledesai, Charuta C, Murru, Siva, Sahoo, Santosh K, Patel, Bhisma K
Format: Artikel
Sprache:eng
Schlagworte:
Acetophenones - chemistry
Amines - chemistry
Bromides - chemistry
Isothiocyanates - chemistry
Sulfhydryl Compounds - chemistry
Thiocyanates - chemistry
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Beschreibung
Zusammenfassung:An unprecedented transfer of a thiocyanate (−SCN) group from aroyl/acyl isothiocyanate to alkyl or benzylic bromide is observed in the presence of a tertiary amine. This process is most effective when the bromomethyl proton is less acidic, while the presence of a more acidic proton gives 1,3-oxathiol-2-ylidine and other related products.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901561j