Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Experiment Videos

The quest for chiral Grignard reagents.

Reinhard W Hoffmann1

  • 1Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany. rwho@chemie.uni-marburg.de

Chemical Society Reviews
|July 24, 2003
PubMed
Summary

Researchers developed a novel chiral Grignard reagent to investigate single electron transfer (SET) in organomagnesium reactions. This chiral probe helps determine the extent of free radical involvement in these crucial chemical transformations.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Research Projects How They Sprout, Bloom, and Wither Away.

Chemical record (New York, N.Y.)·2025
Same author

Overcoming (some) rules in synthesis design.

Chemical Society reviews·2025
Same author

A Case for Bond-Network Analysis in the Synthesis of Bridged Polycyclic Complex Molecules: Hetidine and Hetisine Diterpenoid Alkaloids.

Angewandte Chemie (International ed. in English)·2019
Same author

α-Iodoalkyl-Iodine-Ate Complexes as Observable Intermediates in the Iodine- Magnesium Exchange Reaction.

Angewandte Chemie (International ed. in English)·2018
Same author

α-Chloroalkylmagnesium Reagents of >90 % ee by Sulfoxide/Magnesium Exchange.

Angewandte Chemie (International ed. in English)·2018
Same author

Wittig and His Accomplishments: Still Relevant Beyond His 100th Birthday.

Angewandte Chemie (International ed. in English)·2018

Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms
  • Stereochemistry

Background:

  • Organomagnesium reagents are vital in organic synthesis.
  • Standard preparation methods involve free radicals, complicating mechanistic studies.
  • Detecting single electron transfer (SET) in these reactions requires specialized tools.

Purpose of the Study:

  • To synthesize a chiral secondary Grignard reagent with a unique stereogenic center.
  • To utilize this reagent as a probe for investigating SET in organomagnesium reactions.
  • To elucidate the role of free radicals in the reactivity of organomagnesium compounds.

Main Methods:

  • Asymmetric synthesis of a chiral Grignard reagent (36).
  • Starting material: enantiomerically pure alpha-chloroalkyl-sulfoxide (30b).
  • Key reactions: sulfoxide/magnesium exchange (to 33) and carbenoid homologation.

Main Results:

  • Successful generation of a chiral Grignard reagent (36) with a sole stereogenic center.
  • This reagent serves as an effective probe for SET mechanisms.
  • The study provides insights into the extent of free radical participation.

Conclusions:

  • A novel chiral Grignard reagent was synthesized via asymmetric methods.
  • This reagent is a valuable tool for studying single electron transfer in organomagnesium chemistry.
  • Understanding SET is crucial for controlling reactivity and stereochemistry.

Related Experiment Videos