Related Experiment Video
Updated: Feb 11, 2026

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry
Published on: November 20, 2014
An Unprecedented Elimination-Driven Migration: The Reductive Dihalobornane-Camphene Rearrangement
László Garamszegi1, Manfred Schlosser1
1Institut de Chimie Organique, Université Bâtiment de Chimie (BCh) CH-1015 Lausanne (Switzerland) Fax: (+41) 21-692-39-65.
A novel organometallic Wagner-Meerwein rearrangement has been discovered, involving carbocationic alkyl 1,2-migration. This structural reorganization occurs via a push-pull mechanism, not through carbanionic intermediates.
Area of Science:
- Organometallic Chemistry
- Organic Reaction Mechanisms
Background:
- The Wagner-Meerwein rearrangement is a fundamental carbocationic alkyl 1,2-migration reaction in organic chemistry.
- Understanding its organometallic analogues provides insights into reaction mechanisms and synthetic strategies.
Purpose of the Study:
- To discover and characterize an organometallic counterpart to the Wagner-Meerwein rearrangement.
- To elucidate the mechanism of this novel organometallic rearrangement.
Main Methods:
- The study likely involved synthesis and characterization of specific organometallic compounds.
- Mechanistic investigations using spectroscopic and computational methods were probably employed.
Main Results:
- Discovery of a new organometallic reaction analogous to the Wagner-Meerwein rearrangement.
- Elucidation of a push-pull mechanism, distinct from traditional carbanionic pathways.
- Identification of 1,2-migration occurring through a novel concerted process.
Conclusions:
- This work expands the known scope of Wagner-Meerwein type rearrangements into organometallic chemistry.
- The identified push-pull mechanism offers a new perspective on carbocationic rearrangements.
- This discovery may open avenues for new synthetic methodologies in organometallic chemistry.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Oxidation-Reduction Reactions
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Elimination Kinetics: First-Order and Zero-Order
Drug clearance depends on the rate of drug elimination and its plasma concentration. Another important parameter is a drug's half-life, which is the time required for its concentration to decrease by half. In most cases, drug clearance follows first-order...
Elimination Reactions

