Chemical modification of amide-based catenanes and rotaxanes II. Synthesis of tertiary amine [2]catenanes and [2]rotaxanes via N-methylation followed by borane reduction of secondary amide [2]catenanes and [2]rotaxanes and mobility of their components

Nobuhiro Watanabe, Yoshio Furusho, Nobuhiro Kihara, Toshikazu Takata, Kazushi Kinbara, Kazuhiko Saigo

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22 Citations (Scopus)

Abstract

Secondary amide [2]catenane 1a was converted to the corresponding tertiary amide [2]catenane 1b by repetitive treatment with a methylating system of CH 3I and KOH in DMSO. The amide functions of 1b were reduced with borane in refluxing THF to give the corresponding tertiary amine [2]catenane 1c. Their structures were characterized by NMR, IR, and FAB-MS spectroscopies. An X-ray crystallographic analysis of 1c showed that its solid-state structure was stabilized by a CH-π interaction between the p-xylylene and m-xylylene units, together with a π-π stacking interaction between the two m-xylylene units. A variable temperature 1H NMR study suggested that 1c had components of highly enhanced mobility in CDCl 3, even at lower temperature, although a much weaker interaction, such as the CH-π interaction, existed between their components in solution. Tertiary amine [2]rotaxane 3c was obtained from the corresponding secondary amide [2]rotaxane 3a by a procedure similar to that used for 1a. The 1H NMR spectra indicated that the mobility of the components of 3c is sufficiently high even at lower temperature.

Original languageEnglish
Pages (from-to)149-155
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume74
Issue number1
DOIs
Publication statusPublished - 2001 Jan 1

ASJC Scopus subject areas

  • Chemistry(all)

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