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The potential of tert -butyl hydroperoxide as a reagent in the guanylation of benzoylthioureas in the presence of amines has been evaluated in a systematic study involving substrates bearing N 2 -substituents with different electronic properties. The results show that t BuOOH is a suitable and robust reagent for the synthesis of either N 1 , N 2 , N 3 -tri- and tetrasubstituted or N 1 , N 2 -disubstituted guanidines from N 2 -substituted N 1 -benzoylthioureas and N 1 -benzoylthioureas, respectively. The recrystallised guanylation adducts were readily obtained in good yields and at high purity levels after a simple one-pot reaction procedure. The crystal structures of two novel benzoylguanidines are provided. [ABSTRACT FROM AUTHOR]