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The rearrangement of aminoalkylisothiourea compounds to mercaptoalkylguanidines via a cyclic intermediate. In reaction A the rearrangement of aminopropylisothiourea (compound 2) to mercaptopropylguanidine via a six ring intermediate. Reaction B visualizes the rearrangement of the aminobutylisothiourea (compound 3) to the corresponding mercaptobutylguanidine. This rearrangement does not occur because of the ring-tension in the seven ring intermediate.
