Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts o...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-01, Vol.25 (1), p.194
Main Authors: Potapov, Vladimir A, Musalov, Maxim V, Kurkutov, Evgeny O, Yakimov, Vladimir A, Khabibulina, Alfiya G, Musalova, Maria V, Amosova, Svetlana V, Borodina, Tatyana N, Albanov, Alexander I
Format: Article
Language:English
Subjects:
1-alkenes
2-bromoethyl selenides
2-bromovinyl selenides
Acetonitrile
Adducts
Alkenes
Alkynes
Chloride
cycloalkenes
Equilibrium
Organic compounds
phenylselenenyl bromide
Reagents
Room temperature
Selectivity
Selenides
Selenium
selenium dibromide
selenium dihalides
Stereochemistry
Stereoselectivity
Sulfur
transfer reactions
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with alkenes or cycloalkenes easily exchange SeBr with other unsaturated compounds, including acetylenes, at room temperature, in acetonitrile. Similar alkene-to-alkene and alkene-to-alkyne transfer reactions of the PhSeBr adducts with alkenes or cycloalkenes take place. The supposed reaction pathway includes the selenium group transfer from seleniranium species to alkenes or alkynes. It was found that the efficient SeBr and PhSeBr transfer reagents are Se(CH CH Br) and PhSeCH CH Br, which liberate ethylene, leading to a shift in equilibrium. The regioselective and stereoselective synthesis of bis( -2-bromovinyl) selenides and unsymmetrical 2-bromovinyl selenides was developed based on the SeBr and PhSeBr transfer reactions which proceeded with higher selectivity compared to analogous addition reactions of SeBr and PhSeBr to alkynes under the same conditions.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25010194