Ferrocenyl substituted 1,3-dithiolanes via [3+2]-cycloadditions of thiocarbonyl S-methanides with ferrocenyl/hetaryl thioketones

GRAPHICAL ABSTRACT

ABSTRACT

The aim of the present study was the investigation of the regioselectivity observed in the course of formation of 1,3-dithiolaness via [3+2]-cycloaddition reactions of differently substituted thiocarbonyl S-methanides with ferrocenyl/hetaryl thioketones. The ¹H and ¹³C NMR analyses of crude reaction mixtures proved that the reactions occurred regioselectively and led to sterically crowded 4,4,5,5-tetrasubstituted 1,3-dithiolanes as sole or major products.

KEYWORDS:

• 1,3-Dithiolanes
• thioketones
• ferrocene
• thiocarbonyl S-methanides

Funding

Authors thank the National Science Center (Cracow, Poland) for financial support within the Maestro Grant (Dec-2012/06/A/ST5/00219).