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

New, general, and practical enamine cyclopropanation using dichloromethane.

Chia-Chung Tsai1, I-Lin Hsieh, Tsung-Ting Cheng

  • 1Department of Chemistry, National Chung-Hsing University, Taichung, Taiwan, Republic of China.

Organic Letters
|May 19, 2006
PubMed
Summary

Dichloromethane acts as a novel electrophilic carbene equivalent, readily adding to enamine double bonds. This reaction is tolerant of other alkenes and effective even with sterically hindered ketones using TiCl(4)-Mg.

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

Total Synthesis of (+)-Lycoricidine and Conduramine B-1, <i>ent</i>-C-1, C-4, D-1, <i>ent</i>-F-1, and <i>ent</i>-F-4, and Formal Synthesis of (-)-Laminitol: a <i>C</i><sub>2</sub>-Symmetric Chiral-Pool-Based Flexible Strategy.

The Journal of organic chemistry·2019
Same author

Exceedingly Concise and Elegant Synthesis of (+)-Paniculatine, (-)-Magellanine, and (+)-Magellaninone.

Organic letters·2015
Same author

Influence of bacterial cellulose (nata) on the physicochemical and sensory properties of frankfurter.

Journal of food science·2014
Same author

A C2-symmetric chiral pool-based flexible strategy: synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4-epi-shikimic acids, and (+)- and (-)-pinitol.

The Journal of organic chemistry·2014
Same author

Suppression of allergic reactions in ovalbumin-sensitized mice by yam storage proteins dioscorins.

Journal of agricultural and food chemistry·2013
Same author

Bromoform activation. TiCl4-Mg-promoted CHBr2- and CBr3- transfer to a variety of aldehydes and ketones.

Organic letters·2013

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Enamines are versatile synthetic intermediates.
  • Carbene additions are fundamental organic reactions.
  • Developing new carbene equivalents is crucial for synthetic innovation.

Purpose of the Study:

  • To explore dichloromethane as a novel electrophilic carbene equivalent.
  • To investigate the reactivity of enamines with dichloromethane.
  • To establish reaction conditions for this transformation.

Main Methods:

  • Reaction of various enamines with dichloromethane.
  • Utilizing titanium tetrachloride-magnesium (TiCl(4)-Mg) as a promoter.
  • Analysis of reaction products to confirm carbene addition.

Related Experiment Videos

Main Results:

  • Dichloromethane successfully functioned as an electrophilic carbene equivalent.
  • The addition reaction proceeded efficiently with diverse enamine substrates.
  • Other alkene moieties within the enamine were well tolerated.
  • Enamines derived from sterically hindered ketones showed good reactivity.

Conclusions:

  • Dichloromethane offers a new synthetic route for carbene additions to enamines.
  • The developed method is robust and applicable to challenging substrates.
  • This expands the synthetic utility of dichloromethane in organic synthesis.