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Synthesis and characterization of 3,3,10,10-tetramethyl-1,5,8,12-tetraazacyclotetradecane. A new route to macrocyclic polyamides and polyamines

✍ Scribed by Olivier Siri; Guy Royal; Alain Tabard; Roger Guilard; Volker Hugh; Michael Veith


Publisher
Elsevier Science
Year
1998
Tongue
English
Weight
276 KB
Volume
1
Category
Article
ISSN
1387-1609

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✦ Synopsis


The 1:1 and 2:2 cyclization reactions were simultaneously observed by addition ofdiethyl oxalate on 3,3,10,10-tetramethyl-1,5,8, l 2-tetraazadodecane. The resulting 1 : 1 cyclisation product was fully characterized by spectroscopy and X-ray diffraction study. The reduction of this compound gives the 3,3,10,10tetramethyl-1,5,8,12-tetraazacyclotetradecane with a high yield. ~) Acaddmie des sciences/Elsevier, Paris tetraazamacrocycle / octaazamacrocycle / X-ray Rdsum6 -Synth6se et caract6risation du 3,3,10,10-t6tram6thyl-1,5,8,12-t6traazacyclotdtraddcane. Une nouvelle voie d'acc/~s aux polyamines et polyamides macrocycliques. Les rdactions de cyclisation de type 1:1 et 2:2 sont observdes par action d'oxalat,: de di&hyle sur le 3,3,10,10-t&ram&hyl-1,5,8,12-tdtraazadoddcane. Le produit r&ultant de la cyclisation l:1 a dtd caract&isd par spectroscopie et sa structure rdsolue par une dtude de diffraction X. La rdduction de o: rnSme produit conduit au 3,3,10,10-t&ramdthyl-l,5,8,12-tdtraazacyclotdtraddcane avec un bon rendement. © Acaddmie des sciences/Elsevier, Paris tdtraazamacrocycle / octaazamacrocycle / diffraction X

Version frant;aise abr6g6e

En raison de leurs multiples applications, notamment en chimie de coordination, les voles d'acc& aux macrocycles polyaminds font l'objet de nombreuses dtudes [1]. Cependant, les mdthodes de syn-th~se n&essitent gdn&alement un grand nombre d'&apes et les rendements sont souvent faibles. Parmi les polyazamacrocycles, le cyclame ou 1,4,8,11-t&raazacyclotdtraddcane est trSs utilisd en raison de ses propri&ds complexantes [2-4]. De plus, le cyclame N-ou C-fonctionnalisd peut former des complexes prdsentant des propri&& physico-chimiques tout h fair originales. Ainsi, lorsque le cyclame est C-substitud par des groupements m&hyle en position ~ (4, schdma I), les complexes m&alliques Communicated by Francois MATHEY.


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