Organoselenium chemistry

organoselenium compoundallylic oxidationselenoxideselenoetherseleniumallylic oxidationsallylic oxidativeDimethyl selenide (DMSe)organic selenium compoundsorganoselenium
Organoselenium compounds are chemical compounds containing carbon-to-selenium chemical bonds.wikipedia
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Chalcogen

group 1616chalcogens
Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected.
There are some organic selenium compounds, such as selenoproteins.

Selenol

methylselenolSeH
Selenols are one of the principal classes of organoselenium compounds.

Selenenic acid

In presence of a β-hydrogen, a selenide will give an elimination reaction after oxidation, to leave behind an alkene and a selenenic acid.
A selenenic acid is an organoselenium compound and an oxoacid with the general formula RSeOH, where R ≠ H. It is the first member of the family of organoselenium oxoacids, which also include seleninic acids and selenonic acids, which are RSeO 2 H and RSeO 3 H, respectively.

Selenium

SeSe 3 selenium poisoning
Organoselenium compounds are chemical compounds containing carbon-to-selenium chemical bonds.
Another naturally occurring organoselenium compound is dimethyl selenide.

Seleninic acid

A seleninic acid is an organoselenium compound and an oxoacid with the general formula RSeO 2 H, where R ≠ H. It is a member of the family of organoselenium oxoacids, which also includes selenenic acids and selenonic acids, which are RSeOH and RSeO 3 H, respectively.

Selenourea

selenoureas
Selenourea is the organoselenium compound with the formula SeC(NH 2 ) 2.

Benzeneselenol

selenophenolPhenylselenolSodium benzeneselenolate
There are some limitations associated with the methodologies to prepare vinylic selenides illustrated above; the procedures described employ diorganoyl diselenides or selenophenol as starting materials, which are volatile and unstable and have an unpleasant odor.
Benzeneselenol, also known as selenophenol, is the organoselenium compound with the formula C 6 H 5 SeH, often abbreviated PhSeH.

Sodium selenide

Na 2 Se
With alkyl halides, one obtains a variety of organoselenium compounds:

Dimethyl selenide

dimethylselenide
Trace quantities of dimethyl selenide and allyl methyl selenide are found in human breath after consuming raw garlic.
Dimethyl selenide is the organoselenium compound with the formula (CH 3 ) 2 Se.

Allyl group

allylallylicallyl cation
Specifically, SeO 2 will convert an allylic methylene group into the corresponding alcohol.
Other reactions that tend to occur with allylic compounds are allylic oxidations, ene reactions, and the Tsuji–Trost reaction.

Allyl alcohol

allylic alcoholAllylic alcoholsalcohol
Specifically, SeO 2 will convert an allylic methylene group into the corresponding alcohol.
Allyl alcohols in general can be prepared by allylic oxidation of allyl compounds by selenium dioxide.

Grieco elimination

The Grieco elimination is a similar selenoxide elimination using o-nitrophenylselenocyanate and tributylphosphine to cause the elimination of the elements of H 2 O.
In the second step, the selenide is oxidized with hydrogen peroxide to give a selenoxide.

Chemical compound

compoundcompoundschemical compounds
Organoselenium compounds are chemical compounds containing carbon-to-selenium chemical bonds.

Carbon

Ccarbonaceouscarbon atom
Organoselenium compounds are chemical compounds containing carbon-to-selenium chemical bonds.

Chemical bond

bondbondschemical bonds
Organoselenium compounds are chemical compounds containing carbon-to-selenium chemical bonds.

Oxidation state

oxidation numberoxidation statesoxidation
Selenium can exist with oxidation state −2, +2, +4, +6.

Bond energy

Bond strengthbond energiesstrength
Down the group 16 column, the bond strength becomes increasingly weaker (234 kJ/mol for the C−Se bond and 272 kJ/mol for the C−S bond) and the bond lengths longer (C−Se 198 pm, C−S 181 pm and C−O 141 pm).

Joule

JkJMJ
Down the group 16 column, the bond strength becomes increasingly weaker (234 kJ/mol for the C−Se bond and 272 kJ/mol for the C−S bond) and the bond lengths longer (C−Se 198 pm, C−S 181 pm and C−O 141 pm).

Mole (unit)

molemolmoles
Down the group 16 column, the bond strength becomes increasingly weaker (234 kJ/mol for the C−Se bond and 272 kJ/mol for the C−S bond) and the bond lengths longer (C−Se 198 pm, C−S 181 pm and C−O 141 pm).

Bond length

lengthbond distancebond lengths
Down the group 16 column, the bond strength becomes increasingly weaker (234 kJ/mol for the C−Se bond and 272 kJ/mol for the C−S bond) and the bond lengths longer (C−Se 198 pm, C−S 181 pm and C−O 141 pm).

Acid dissociation constant

p''K'' a pKapK a
The pK a values of XH 2 are 16 for oxygen, 7 for sulfur and 3.8 for selenium.

Sulfoxide

sulfoxidessulfinylS''-oxide
In contrast to sulfoxides, the corresponding selenoxides are unstable in the presence of β-protons and this property is utilized in many organic reactions of selenium, notably in selenoxide oxidations and in selenoxide eliminations.

Organic reaction

organic reactionsreactionsorganic
In contrast to sulfoxides, the corresponding selenoxides are unstable in the presence of β-protons and this property is utilized in many organic reactions of selenium, notably in selenoxide oxidations and in selenoxide eliminations.

Alcohol

alcoholssecondary alcoholtertiary alcohol