Organoselenium chemistry



Organoselenium compounds are group 16 elements and similarities in chemistry are to be expected.

Selenium can exist with organic reactions of selenium, notably in selenoxide oxidations and in selenoxide eliminations.

The first organoselenium compound ever isolated was diethylselenide in 1836.[4]

Selenium compounds

Selenols RSeH are the selenium equivalents of alcohols and phenylmagnesium bromide and elemental selenium with aqueous acidic workup.

Diselenides R-Se-Se-R are the selenium equivalents of disulfides and used in organic chemistry as starting compounds for selenols and selenenyl halides R-Se-Cl or R-Se-Br.

Selenides R-Se-R are the selenium equivalents of carbanion is stabilized by the unfilled selenium 4d orbital. This ate complex collapses back to a selenide but with exchange of ligands as in R'-se-Se.

Selenoxides R-Se=O-R are the selenium equivalents of sulfones with sulfur replaced again by selenium.

Selenoxide oxidations

Allylic oxidation is an organic oxidation converting an oxidizing agents that can bring about this reaction.

This type of reaction often involves sigmatropic reaction.

Oxidations involving selenium dioxide are often carried out with catalytic amounts of the selenium compound and in presence of a sacrificial catalyst or co-oxidant such as pyridinium chlorochromate are other oxidizing reagents.

The type of substrate can be extended to α-carbonyl compounds such as ketones converting them to diketones

Selenoxide eliminations

In presence of a β-proton, a selenide will give an enones.

The Grieco elimination is a similar selenoxide elimination with o-nitrophenylselenocyanate and tributylphosphine.

Deselenation

The three-membered seleniranes are related to the oxygen pendants alkenes. This property has been utilized in synthetic organic chemistry [5].

See also

  • The chemistry of carbon bonded to other elements in the periodic table:
CH He
CLi CBe CB CC CN CO CF Ne
CNa CMg CAl CSi CP CS CCl Ar
CK CCa CSc CTi CV CCr CMn CFe CCo CNi CCu CZn CGa CGe CAs CSe CBr Kr
CRb CSr CY CZr CNb CMo CTc CRu CRh CPd CAg CCd CIn CSn CSb CTe CI Xe
CCs CBa CHf CTa CW CRe COs CIr CPt CAu CHg CTl CPb CBi CPo CAt Rn
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Uub Uut Uuq Uup Uuh Uus Uuo
↓
La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
Ac Th Pa CU Np Pu Am Cm Bk Cf Es Fm Md No Lr


carbon
Core organic chemistry many uses in chemistry.
Academic research, but no widespread use Bond unknown / not assessed.

References

  1. ^ A. Krief, L. Hevesi, Organoselenium Chemistry I. Functional Group Transformations., Springer, Berlin, 1988 ISBN 0-387-18629-8
  2. ^ S. Patai, Z. Rappoport (Eds.), The Chemistry of Organic Selenium and Tellurium Compounds, John. Wiley and Sons, Chichester, Vol. 1, 1986 ISBN 0-471-90425-2
  3. ^ Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Baldwin, J. E., Ed.; Pergamon Books Ltd.: New York, 1986 ISBN 0-08-032484-3
  4. ^ Lwig, C. J. Pogg. Ann. 1836, 37, 552
  5. ^ Developments in the chemistry of selenaheterocyclic compounds of practical importance in synthesis and medicinal biology Arkivoc 2006 (JE-1901MR) Jacek Młochowski, Krystian Kloc, Rafał Lisiak, Piotr Potaczek, and Halina Wójtowicz Link
 
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