Synthesis of C3-Symmetrical 1,3,5-Tris-Protected Calix[6]arene-Based Molecular Platforms
Martin Lepeintre1,2, Julie Champciaux2, Benoit Colasson1
1Université Paris Cité, CNRS, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, F-75006 Paris, France.
Abstract:
Few synthetic methodologies that yield tris-functionalized C3-symmetrical calix[6]arenes have been reported. In this work, three allyl protecting groups are selectively placed in 1,3,5 alternate positions of three pristine calix[6]arenes, each differing by their substituent on the large rim, resulting in three new C3-symmetrical molecular platforms. Removal of the protecting allylic groups gives access to sophisticated calix[6]arenes that can be further modified. The potential of these new C3-symmetrical molecular platforms is notably exemplified through the development of a new family of calix[6]arene-based N ligands.
Related Concept Videos
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...


