How do you go from an alkene to an epoxide?

Treating an alkene with a “peroxyacid” (that’s a carboxylic acid containing an extra oxygen) leads to direct formation of an epoxide. A popular peroxyacid for this purpose is m-CPBA [m-chloroperoxybenzoic acid], although other peroxyacids of the general form RCO3H also find use.

Which reagent can be used to convert an alkene to an epoxide?

Peroxycarboxylic acids, which are more electrophilic, convert alkenes to epoxides without the intervention of metal catalysts. In specialized applications, other peroxide-containing reagents are employed, such as dimethyldioxirane.

How do you convert alkenes to diols?

Dihydroxylation is the process by which an alkene is converted into a vicinal diol. Although there are many routes to accomplish this oxidation, the most common and direct processes use a high-oxidation-state transition metal (typically osmium or manganese).

Is epoxidation an oxidation reaction?

Epoxidation is the chemical reaction which converts the carbon–carbon double bond into oxiranes (epoxides), using a variety of reagents including air oxidation, hypochlorous acid, hydrogen peroxide, and organic peracid (Fettes, 1964).

How is an alkene converted to an epoxide?

The epoxidation reaction is where an alkene is subjected to a peroxyacid to convert it into an epoxide. Another way to say it is epoxidation is the electrophilic addition of oxygen to the double bond of the alkene. 3) What reagents can you use to create the epoxide? Generally, peroxy acids are used in this electrophilic addition to the alkene.

How is the stereochemistry of epoxides determined?

The epoxidation is a syn addition, and the stereochemistry of the product is determined based on the structure of the alkene. Cis alkenes give cis epoxides, and trans alkenes give trans epoxides.

When do cis alkenes give trans epoxides?

Cis alkenes give cis epoxides, and trans alkenes give trans epoxides. Remember, when the stereochemistry of the product is dictated by the stereochemistry of the substrate, the reaction is said to stereospecific, i.e. it has no choice- cis gives cis, trans gives trans regardless of their stability.

Why does oxacyclopropane have the same stereochemistry as the alkene?

Since the transfer of oxygen is to the same side of the double bond, the resulting oxacyclopropane ring will have the same stereochemistry as the starting alkene. A good way to think of this is that the alkene is rotated so that some constituents are coming forward and some are behind. Then, the oxygen is inserted on top.