6533b827fe1ef96bd12853ea
RESEARCH PRODUCT
New Synthesis oftrans-Disubstituted Cyclam Macrocycles – Elucidation of the Disubstitution Mechanism on the Basis of X-ray Data and Molecular Modeling
Slimane DahaouiGuy RoyalAlain TabardV. Dahaoui-gindreyPluton PullumbiRoger GuilardClaude Lecomtesubject
chemistry.chemical_compoundMolecular modelchemistryMechanism (philosophy)StereochemistryOrganic ChemistryCyclamX ray dataReactivity (chemistry)Physical and Theoretical ChemistryHexadecaneCombinatorial chemistrydescription
A new way to synthesize trans-disubstituted cyclam tetraazamacrocycles 1 is reported. The synthesis proceeds in three steps via the tricyclic 1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane system 2, which can be selectively dialkylated and hydrolyzed under basic conditions to give the final product 1. An understanding of the reactivity, based on the X-ray experimental electrostatic potential and molecular modeling of the 1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane macrotricycle, has permitted the elucidation of a new reaction pathway leading to the trans-disubstituted cyclam.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1998-09-01 | European Journal of Organic Chemistry |