cyclen

Also known as 1,4,7,10-tetrazacyclododecane, [12]aneN₄

Cyclen (1,4,7,10-tetraazacyclododecane) is an aza-crown ether with the formula (CH2CH2NH)4. It is a white solid. It forms coordination complexes with metal cations and is used to synthesize the chelating agent DOTA which has several medical applications. Being structurally simple, symmetrical, and polyfunctional, cyclen has been widely investigated.

~2 min read

Encyclopedic overview

5 sections

Contents

Synthesis
Coordination complexes
Related compounds
References
Further reading

== Synthesis == Some syntheses exploit the Thorpe-Ingold effect to facilitate ring-formation. Illustrative is the reaction of the deprotonated tosylamides with ditosylates: TsN(CH2CH2NTsNa)2 + TsN(CH2CH2OTs)2 → (TsNCH2CH2)4 The resulting macrocycle can be deprotected with strong acid. Base gives the tetramine.

Excerpted from Wikipedia’s “cyclen” article, available under the CC BY-SA 4.0 licence.