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Nitration of thiacalix[4]arene derivatives

✍ Scribed by Pavel Lhoták; Jiri Svoboda Jr.; Ivan Stibor; Jan Sykora

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 205 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01667-2

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✦ Synopsis

A direct nitration of the upper rim of thiacalix [4]arenes is not possible due to the undesirable oxidation of the sulphur atoms during the nitration step leading to very complicated reaction mixtures. On the other hand, thiacalix[4]arene derivatives can be at first transformed intentionally to the highest oxidation state-sulfones, and subsequently ipso-nitrated using 100% HNO 3 in CF 3 COOH. This procedure gives smoothly mono-or dinitro-derivatives in acceptable yields which opens the way for further derivatisation of the upper rim of thiacalixarenes.

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