Synthesis of novel paracyclophanes with linear P,N-containing spacers |
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Authors: | S N Ignat’eva A S Balueva A A Karasik D V Kulikov A V Kozlov Sh K Latypov P Lönnecke E Hey-Hawkins O G Sinyashin |
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Institution: | (1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation;(2) Institute of Inorganic Chemistry, Leipzig University, 29 Johannisallee, D-04103 Leipzig, Germany |
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Abstract: | Condensation of bis(hydroxymethyl)mesityl-and bis(hydroxymethyl)phenylphosphines with N,N′-disubstituted bis(4-aminophenyl)methanes and bis(4-amino-3-carboxyphenyl)methane occurred as covalent self-assembly spontaneously
giving a mixture of trans-and cis-diastereomers of 1,5,19,23-tetra-R′-3,21-di-R-1,5,19,23-tetraaza-3,21-diphospha5.1.5.1]paracyclophanes as the major products.
The trans-isomer (R is mesityl; R′ is methyl) was isolated in the individual state and structurally characterized by X-ray diffraction
analysis. Sulfurization of macrocyclic diphosphines (R = Ph; R′ is 3-pyridylmethyl or 4-pyridylmethyl) gave the corresponding
diphosphine disulfides, the trans-stereoisomer being isolated in the individual state.
Dedicated to Academician G. A. Abakumov on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1765–1774, September, 2007. |
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Keywords: | phosphorus-containing cyclophanes bis(hydroxymethyl)phenylphosphine bis(hydroxymethyl)mesitylphosphine N N′ -disubstituted bis(4-aminophenyl)methanes bis(4-amino-3-carboxyphenyl)methane condensation covalent self-assembly |
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