The treatment of mono- and tetra-thiacalixarenes (2, 3) with chloramine T gave unexpected monospirodienone derivatives (4, 5). The reaction of methyl ethers (6, 7) of thiacalixarenes with chloramine T followed by demethylation gave novel derivatives (10, 11) having a sulfilimine group. X-ray analysis revealed that 11 adopts cone conformation in the solid state, in which the sulfilimine group directs toward axial orientation to take part in circular hydrogen bonding with four OH groups.
ASJC Scopus subject areas
- Organic Chemistry