Alkyl-and arylsulfanyl-substituted unsaturated carbonyl compounds

ABSTRACT

A method for the synthesis of captodative sulfanyl enals, enones and enoates via nucleophilic vinylic substitution of corresponding halogen-bearing derivatives has been developed. The one-pot treatment of the haloenoates, haloenones or haloenals with thiols in the presence of organic base leads either to vicinal dithiosubstituted carbonyl-bearing compound or captodative systems with good to excellent yield. The major reaction direction strongly depends on the type of base used.

GRAPHICAL ABSTRACT

KEYWORDS:

• Thiols
• nucleophilic vinylic substitution
• thia-Michael
• unsaturated sulfides
• halogenophilic reaction

Acknowledgements

Spectroscopic and analytical data were obtained using instrumentation in the Baykal Analytical Center for Collective Use SB RAS.

Disclosure statement

No potential conflict of interest was reported by the authors.