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-oxathiol-2-ylidine and other related products.
Palsuledesai
Charuta C
CC
Department of Chemistry, Indian Institution of Technology Guwahati, Guwahati 781 039, India.
Murru
Siva
S
Sahoo
Santosh K
SK
Patel
Bhisma K
BK
D000098:Acetophenones / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013861:Thiocyanates / Q000737:chemistry*
D000098:Acetophenones; D000588:Amines; D001965:Bromides; D017879:Isothiocyanates; D013438:Sulfhydryl Compounds; D013861:Thiocyanates; C008730:oxathiol