Functionalized Macrocycles from Functionalized Tetra-Amines: Pendent-Arm Macrocycles Derived from Dichloropivalic Acid

P.V. Bernhardt, J.M. Harrowfield, Y. Kim, George Koutsantonis, Y.H. Lee, P. Thuery

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

Reaction between ethane-1,2-diamine and 3,3'-dichloropivalic acid results in different, isomeric tetra-amine derivatives, one a tetraamino carboxylic acid and the other a carboxamidotriamino alcohol, depending upon reaction conditions, Intended conversion of the Cu(II) complex of the former to a cyclam-like macrocycle through reaction with nitroethane and formaldehyde results in isolation of derivatives of both the former and the latter. This can be rationalized by assuming the intermediacy of an azetidinone, a species similar to that seen in simpler reactions of dichloropivalates. A single reaction thereby provides pendent-arm macrocycles where one has an electrophilic and the other a nucleophilic substituent. Parallel chemistry is not seen in the reaction between propane-1,3-diamine and 3,3'-dichloropivalate.
Original languageEnglish
Pages (from-to)1681-1688
JournalInorganic Chemistry
Volume43
Issue number5
DOIs
Publication statusPublished - 2004

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