Organotin mediated cycloaddition reactions: a re-investigation of the reaction between organotin azides and isothiocyanates

Article abstract of DOI:10.1016/0022-328X(92)80092-C

Organotin derivatives of 1-organo-5-thiotetrazole (RN4CS) have been synthesized by two methods: (i) a cycloaddition reaction between Bu3SnN3 and RNCS, and (ii) reaction between the sodium salt of the preformed tetrazole and an organotin halide.The structure of Bu2Sn(SCN4Ph)2 has been determined, and the ligand shown to be in the thio form, attached to tin through sulphur, rather than through nitrogen as previously reported.An analysis of the azide-isothiocyanide cycloaddition reaction based upon molecular orbital calculations is presented.