Bromination of stilbene

Stilbene is one of the gain mediums used in dye lasers. Many stilbene derivates stilbenoids are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.

Bromination of stilbene

Besides avoiding use of solvents, the experimental design is not dependent upon the densities of the reactants and the procedure generates little or no waste while providing the reaction products in high yield and in high purity.

Bromination of stilbene

In a test tube, a liquid perfluoroalkane acts as a phase screen to separate the two reactants, one of which is more dense than the screen and the other one that is less dense.

If both reactants are less dense than the phase screen, one can carry out the reaction in a U-tube Bromination of stilbene if both reactants are denser than the screen, the reaction can be carried out in an inverted U-tube. As the reagent diffuses through the perfluoroalkane, it reaches the substrate and reacts with it.

In addition, some solvents, reagents and reaction products are partially soluble in FC [ 13 — 16 18 ], which limits our ability to either reuse or recycle it.

Ryu and Curran have reported benefits in using heavier liquid perfluoro compounds as phase screens [ 19 ].


PTFE offers some advantages compared to a liquid perfluoro phase screen: PTFE tape is inexpensive, easy to use and may be reused. In addition, experimental design is not dependent upon densities of the reactants. However, in some cases, such as when iodine monochloride was used as a reagent or when insoluble products formed an impermeable barrier on the PTFE tape, this method was not suitable.

To address the described shortcomings and to make the design more environmentally friendly, we have developed solvent-free PV-PTFE reactions. Neat substrate was placed in the flask and a PTFE-sealed tube filled with the reagent was placed into the vapor phase above it. A thermometer adapter, with a reagent delivery tube in place of thermometer, was used for this purpose.

A loaded tube inserted into an empty closed flask could be stored for a future use for several days as long as there were no leaks.

Bromination of stilbene

There was equilibrium between the liquid reagent in the tube and its vapors in the flask. The reagent diffused through PTFE tape only if the vapors were consumed or removed e.

Todd:Chem3x11 ToddL8 - OpenWetWare Bromination of Stillbene - My name is BondCovalent Bond Green Bromination of Stilbene Introduction Bromination is the chemical process by which an alkene is halogenated with bromine. In the case of this experiment E-stilbene is halogenated to form 1,2-dibromo-1,2- dibenzylethane or dibromostilbene.

When a substrate, which consumes the reagent vapors, is placed in the reaction vessel, the reagent rapidly diffuses out of the tube as its vapors are consumed. With the reactions that evolve gases HCl, HBrone should provide an appropriate outlet and possibly a gas trap additional details are provided in Supporting Information File 1.

Stereochemistry of Bromine Addition to an Alkene

A gas outlet was useful even when there was no evolution of a gas as sometimes there was a drop in pressure as a volatile substrate reacted to give a non-volatile product.Material Safety Data Sheet trans-Stilbene MSDS# Section 1 - Chemical Product and Company Identification MSDS Name: trans-Stilbene Catalog.

The bromine adds such that one bromine is added to one carbon and one to the other (a 1,2-addition) and the reagent we add (bromine) is seeking out the electrons of the double bond, meaning we refer to this as an electrophilic addition (unlike when a nucleophile adds to a carbonyl group, which is a nucleophilic addition).

a greener bromination of stilbene Kenyon College – CHEM – Organic Chemistry Lab II For the background and mechanism of the experiment read Mayo, Experiment A2 b (p). Bromination of trans- Stilbene to form 1,2- Dibromo- 1,2-diphenylethane Abstract 1,2-dibromo-1,2-diphenylethane was produced by the bromination of trans-stilbene through the addition of hydrobromic acid (HBr) and hydrogen peroxide (H2O2).

Associated Data

Bromination of (E)-Stilbene & Synthesis of Diphenylacetylene Bromination of an alkene is an example of an electrophilic addition reaction.

Because of their various photophysical and photochemical properties, stilbene compounds can be used in various. Oct 28,  · Bromination And Elimination 1. Diphenylacetylene from Stilbene 2. Overview Dibromide Alkyne Alkene Addition Elimination X 2.

Bromination of Stillbene - My name is BondCovalent Bond