A Practical Route to Cyclobutanols and Fluorocyclobutanes

1-[(Ethoxycarbonothioyl)sulfanyl]cyclobutyl acetate (xanthate 7) was found to add electronically unbiased alkenes and certain heteroarenes. In the latter case, this corresponds a variant of Minisci reaction allows late-stage modification biologically active substances. Saponification furnishes corresponding cyclobutanols, which, in case nicotine adduct, can be converted into fluorocyclobutanes by action DAST. Fluorocyclobutyl substituted aromatics heteroaromatics are increasingly present drug candidates. Heating acetoxycyclobutyl derivative caffeine with TFA gives rise cyclobutene analogue. Finally, O-ethyl S-[1-(2,2,2-trifluoroethoxy)cyclobutyl] carbonodithioate, obtained unexpectedly while optimizing synthesis xanthate 7, is very promising reagent for introduction rare 2,2,2-trifluoroethoxycyclobutyl motif.