Synthesis and structural analysis of 1,1,2-trichloro-2-[2-chloro-2-(organylsulfanyl)ethenyl]cyclopropanes: NMR, X-ray diffraction and QTAIM approach

Abstract A range of novel 1,1,2-trichloro-2-[2-chloro-2-(organylsulfanyl)ethenyl]cyclopropanes 2a-f were synthesized by reaction of (2-chloroprop-1-en-3-yl)sulfides with dichlorocarbene generated from CHCl 3 . The process apparently proceeds via carbenylation of sulfur atom followed by 2,3-sigmatropic rearrangement with subsequent dehydrochloration and cyclopropanation of the terminal double bond. The resulted trichlorocyclopropane derivatives were studied by 1 H and 13 C NMR spectroscopy as well as X-ray single-crystal analysis that revealed intramolecular CH-π interaction and the formation of intermolecular halogen bonds.