Benzylthia-bridged carceplex

Carceplexes have also been synthesized using templates from cavitands with functionalities other than phenols. Cram synthesized benzylthia-bridged carceplex 13 guest through the shell-closure reaction between tetra(benzyl chloride) cavitand 11 and tetra-benzylthiol cavitand 12 in the solvents 2-butanone, 3-pentanone, ethanol/benzene (1 2), dimethylformamide (DMF), methanol/benzene (2 1), and acetonitrile/benzene (2 1), yielding carceplexes 13-2-butanone, 13-3-pentanone, 13-ethanol, 13-DMF, 13-2 methanol, and 13-2 MeCN respectively (Scheme 4-6) [22]. Technically, 13-2 MeCN is a hemicarceplex, as one acetonitrile molecule was found to escape the interior of the host via a billiard-ball effect, leaving 13-MeCN when heated in toluene [22]. The forma-... 

Scheme 4-6 Synthesis of benzylthia-bridged carceplex 13 guest.

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