Related Experiment Video
Updated: Apr 28, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A strategy utilizing a recyclable macrocycle transporter for the efficient synthesis of a triazolium-based
Sovy Chao1, Camille Romuald, Karine Fournel-Marotte
1Supramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS, UM1-UM2, Université Montpellier 2, Place Eugène Bataillon, case courrier 1706, Bât 17, 3ème étage, 34095 Montpellier Cedex 5 (France) http://www.glycorotaxane.fr.
Abstract:
A general synthesis of triazolium-containing [2]rotaxanes, which could not be accessed by other methods, is reported. It is based on a sequential strategy starting from a well-designed macrocycle transporter which contains a template for dibenzo-24-crown-8 and a N-hydroxysuccinimide (NHS) moiety. The sequence is: 1) synthesis by slippage of a [2]rotaxane building-block; 2) its elongation at its NHS end; 3) the delivery of the macrocycle to the elongated part of the axle by an induced translational motion; 4) the contraction process to yield the targeted [2]rotaxane and recycle the initial transporter.
Related Concept Videos
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
01:17Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.