Acid- and Base-Promoted Rearrangements of Cycloalkane-Fused Heterocycles

Abstract

Certain cycloalkane-anellated heterocycles undergo rearrangement under basic or acidic conditions via ring-contraction, ringexpansion or ring-opening pathways to afford new or unusual compounds. The reactivities and properties of cycloalkane-fused heterocycles differ significantly from those of heteroaromatic ring systems. Possible mechanisms are also discussed.

Deprotonation of resorcinarenes by mono- and diamine bases: complexation and intermolecular interactions in the solid state

“…3,21 Acids and bases have a long history of being constantly used as catalysts in a wide variety of synthetic processes. [22][23][24][25][26] Amines are very common bases used in many catalytic processes. 22 A good example is the use of amines as bases in the alkylation and acylation of resorcinarenes leading to cavitands, carcerands, hemicarcerands and velcrands.…”