N-Substitution Reactions of 1-Substituted Tetrazoline-5-thiones

N- vs. S-Substitution reactions of 1-substituted tetrazoline-5-thiones with various allyl or benzyl halides were studied in order to find effective conditions for N-substitution reactions. When allyl or benzyl halides were reacted with 1-substituted tetrazoline-5-thiones in the presence of TMSI or $BF_3{\cdot}OEt_2$ (or other Lewis acids), N-substitution at 4-position in addition to S-substitution occurred. Reactions were performed either with or without a solvent such as dioxane or propionitrile in the presence of potassium iodide.