Related Experiment Video
Updated: Aug 22, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Three-carbon ring expansion by cyclopropane insertion: macrocyclic musks from readily available C-12 starting
Georg Rüedi1, Matthias Nagel, Hans-Jürgen Hansen
1Organisch-chemisches Institut der Universität, 8057 Zürich, Switzerland. georg@access.unizh.ch
Abstract:
A thermal three-carbon ring expansion based on side chain ring insertion of a cyclopropane moiety is described. Flash vacuum pyrolysis (FVP) of 1-cyclopropyl-cycloalk-3-enol derivatives leads to the three-carbon ring expanded enones with clean retention of double bond geometry. Substrates bearing methyl groups on the cyclopropane ring undergo regioselective bond cleavage, allowing for the systematic preparation of selectively substituted macrocyclic musks from low-priced C-12 starting compounds.
Related Concept Videos
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation

![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)