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Abstract:
The literature synthesis of 9-oxabispidine [OC6H10(NH)2, C] has been
revisited and optimized, which includes determination of the crystal structures of C, the
secondary component trans-(PhSO2)NC4H6O(CH2I)2 (trans-III), and the unexpected solute
intermediate OC6H10(NSO2Ph)2·
1
/2py (V·
1
/2py). The reaction of (1,5-hexadiene)platinum
dichloride with C yields {OC6H10(NH)2}PtCl2 (C1), which is converted to {OC6H10(NH)2}-
Pt(cbdca)·5H2O (C2) and {OC6H10(NH)2}Pt(C2O4) (C3). In the crystal, C1 forms a planar
2D network by N−H··Cl and N−H··O hydrogen bonding. In the crystal structure of C2,
which is isomorphous to the parent bispidine compound (A2), all complex molecules are
encapsulated by a water shell. While complexes C1 and C3 are virtually insoluble in water, C2
dissolves quite well. The low cytotoxicity of compounds C1−C3 is explained by an increased polarity of the bonds in the C
skeleton as a consequence of the electronegative O atom.
