eCite Digital Repository

A Direct Assembly Approach to the Synthesis of N,N'-Bridged Calix[4]pyrroles: The Synthesis of a 1,5-Diazacyclononatriene Locked in a Saddle Conformation

Citation

Wang, J and Gardiner, MG and Herrmann, WA, A Direct Assembly Approach to the Synthesis of N,N'-Bridged Calix[4]pyrroles: The Synthesis of a 1,5-Diazacyclononatriene Locked in a Saddle Conformation, Supramolecular Chemistry, 17, (5) pp. 401-408. ISSN 1061-0278 (2005) [Refereed Article]

DOI: doi:10.1080/10610270500147830

Abstract

Ring closure of 1,2-bis(1-pyrrolylmethyl)benzene in the acid-catalysed condensation with acetone yields the 1,5-diazacyclononatriene [o-C 6H 4(CH 2NC 4H 3-2) 2C(CH 3) 2] as the sole identifiable product. The twisted or saddle conformation of the 1,5-diazacyclononatriene, which was confirmed by X-ray crystal structure determination, is conformationally rigid in solution. The conformation of the 1,5-diazacyclononatriene prevents the formation of the target N,N′-bridged calix[4]pyrrole by further acid-catalysed condensation with acetone, the reaction affording unidentified oligomers/polymers instead. The acid-catalysed condensation of 1,3- and 1,4-bis(1-pyrrolylmethyl)benzene with acetone also yields unidentified oligomers/polymers. © 2005 Taylor & Francis Group Ltd.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:f-Block Chemistry
Objective Division:Manufacturing
Objective Group:Industrial Chemicals and Related Products
Objective Field:Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)
Author:Wang, J (Dr Jun Wang)
Author:Gardiner, MG (Associate Professor Michael Gardiner)
ID Code:32965
Year Published:2005
Deposited By:Chemistry
Deposited On:2005-08-01
Last Modified:2007-11-01
Downloads:0

Repository Staff Only: item control page