trans-2-Aminocyclopentanethiol condenses with formaldehyde to give rel-(3aR,6aR,9aR,1 2aR)-6,12-methanoperhydrodicyclopentano [d,i][1,6,3,8]dithiadiazecine whereas trans-2-aminocyclohexanethiol and trans-2-aminocycloheptanethiol give 1 : 1 mixtures of diastereoisomeric bis(perhydrocycloalkanothiazol-3-yl) methanes.
P. M. R. Barkworth and T. A. Crabb, J. Chem. Soc., Perkin Trans. 1, 1982, 2777 DOI: 10.1039/P19820002777
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