A New Synthetic Method for (Aza)n[3n]cyclophanes by Diethyl Phosphoramidates

Hiroyuki Takemura; Gang Wen; Teruo Shinmyozu

doi:10.1055/s-2005-872171

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Synthesis 2005(17): 2845-2850
DOI: 10.1055/s-2005-872171

PAPER

A New Synthetic Method for (Aza)_n[3ⁿ]cyclophanes by Diethyl Phosphoramidates

Hiroyuki Takemura*^a, Gang Wen^b, Teruo Shinmyozu^b
^a Department of Chemistry, Faculty of Science, Kyushu University, Ropponmatsu 4-2-1, Chuo-ku, Fukuoka, 810-8560 Japan
Fax: +81(92)7264755; e-Mail: takemura@chem.rc.kyushu-u.ac.jp;
^b Institute for Materials Chemistry and Engineering, Kyushu University, Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan
Fax: 81(92)6422735; e-Mail: shinmyo@ms.ifoc.kyushu-u.ac.jp;

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Publication History

Received 14 March 2005
Publication Date:
12 August 2005 (online)

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Abstract

(Aza)_n[3ⁿ]cyclophanes are synthesized by the N-alkylation of diethyl phosphoramidates with bis(bromomethyl)arenes under phase-transfer conditions or anhydrous conditions in the presence of an appropriate base. The method affords N-(diethoxyphosphoryl)(aza)_n[3ⁿ]cyclophanes in moderate yields and can be applied to the synthesis of various types of azacyclophanes. The N-phosphorylated cyclophanes are highly soluble in organic solvents and the diethoxyphosphoryl groups are readily cleaved under acidic conditions to give the corresponding secondary amines.

Key words

cyclophanes - phosphorylations - amines - host-guest systems - macrocycles

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