Related Experiment Video
Updated: Apr 22, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
A fast, efficient and simple method for the synthesis of cyclic alkenyl fluorides by a fluorinative carbocyclization
Pedro Alonso1, Pilar Pardo, Francisco J Fañanás
1Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, Julián Clavería 8, 33006-Oviedo, Spain. fjfv@uniovi.es frodriguez@uniovi.es.
Abstract:
A simple transformation of alkynol or enyne derivatives into cyclic alkenyl fluorides by using tetrafluoroboric acid as the proton and fluoride source is reported. This study includes the first biomimetic cationic cyclization/nucleophilic fluorination reaction of polyenyne derivatives to give terpenoid derivatives.
More Related Videos
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.
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
Base-Promoted α-Halogenation of Aldehydes and Ketones

