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Updated: Aug 23, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Triflamidation of Allyl-Containing Substances:Unusual Dehydrobromination vs. Intramolecular Heterocyclization
Anton S Ganin1, Mikhail Yu Moskalik1, Ivan A Garagan1
1A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia.
This study details the synthesis of halogen-substituted amidines from allyl compounds and triflamide. Brominated amidines are key intermediates, yielding conjugated systems and imidazolidines.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Triflamide is a versatile reagent in organic synthesis.
- Halogenated amidines are important synthetic intermediates.
Purpose of the Study:
- To explore the reaction of allyl compounds with triflamide under oxidative conditions.
- To investigate the synthesis and transformations of halogen-substituted amidines.
Main Methods:
- Oxidative conditions using N-bromosuccinimide (NBS).
- Reactions involving allyl halides, allyl cyanide, and allyl alcohol with triflamide.
- Base-induced dehydrobromination and cyclization reactions.
Main Results:
- Halogen-substituted amidines were successfully synthesized from various allyl precursors.
- Solvent-dependent regioselectivity was observed in the bromotriflamidation of allyl cyanide.
- Dehydrobromination led to conjugated systems, and bromo-substituted amidines formed imidazolidines.
Conclusions:
- Allyl compounds react with triflamide to yield valuable halogenated amidine intermediates.
- The synthetic utility of these amidines was demonstrated through subsequent transformations.
- Bromo-substituted amidines offer unique reactivity compared to their iodo-analogs.
Related Concept Videos
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Radical Substitution: Allylic Bromination
Radical Substitution: Allylic Chlorination
Formation of Halohydrin from Alkenes
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

