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Introduction
1.3.3 Disulfide exchange
Disulfide exchange has been thoroughly investigated in generation of DCLs. 24-38 Otto et al.
reported the generation of a DCL having cage-like structures made from di- and trithiols 28-30
under thermodynamic control (Figure 1.7). 38 The interlocked disulfides 31-33 form by oxidation
of an aqueous solution of the thiols upon exposure to air in the presence of a thiolate. Quenching
of the DCL took place under acidic condition or by removing the thiolate. 39
Figure 1.7 DCLs of water soluble disulfide linked cages.
1.3.4 Acetal exchange
There are few examples reported in literature, which describe generation of DCC from
acetals. 40,41 Mandolini and co-workers reported on the acid-catalyzed transacetalation reaction of
formaldehyde acetals with generation of a DCL of interchangeable cyclophane-type oligomers
under mild conditions. 42-45 The authors suggested the mechanism shown in Figure 1.8 for the
transacetalation process, which took place through a ring-fusion/ring-fission S N 2 pathway.
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