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Synthesis 2005(17): 2845-2850
DOI: 10.1055/s-2005-872171
DOI: 10.1055/s-2005-872171
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New Synthetic Method for (Aza)n[3n]cyclophanes by Diethyl Phosphoramidates
Further Information
Received
14 March 2005
Publication Date:
12 August 2005 (online)
Publication History
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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