Organotellurium chemistry

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Organotellurium chemistry in chemistry describes the synthesis and properties of chemical compounds containing a carbon to tellurium chemical bond [1]. Organotellurium chemistry was developed in the wake of organoselenium chemistry and sharing the same group in the periodic table both chemistries have much in common. The field receives academic interest but organotellurium compounds rarely venture outside the laboratory.

Diphenyl ditelluride is used as a TePh source in organic synthesis. Dimethyl telluride is highly toxic and as a product of microbial metabolism first discovered in 1939. it is used in Metalorganic vapour phase epitaxy. Commonly used tellurium based reagents are hydrogen telluride, NaHTe, sodium telluride, PhTeH and PhTeNa.

Reactions with these reagents are:

Another type is this Stille reaction [3]:
cross-coupling of organotellurium compounds with organostannanes
  • Hydrotelluration: Compounds of the type RTeH react with alkynes R'CCH to R'HCCTeR with anti addition to a Z-alkene. In contrast hydrostannylation, hydrozirconation and hydroalumination in similar reactions react with syn addition.
  • Te/Li exchange in transmetallation [4] is used in the synthesis of lithium reagents with demanding functional groups.
  • Allylic oxidation: like the selenium counterpart selenoxide oxidation, allylic telluroxides undergo [2,3]-sigmatropic rearrangements forming allylic alcohols after hydrolysis.
  • Olefin synthesis: Like the selenium counterpart selenoxide elimination, certain telluroxides (RTeOR) can form alkenes on heating.

[edit] 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 CCe 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


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

[edit] References

  1. ^ Organometallic Reagents for Synthetic Purposes: Tellurium Nicola Petragnani, and Wai-Ling Lo J. Braz. Chem. Soc., Vol. 9, No. 5, 415-425, 1998 http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000500002.
  2. ^ For an example see: Organic Syntheses, Coll. Vol. 6, p.468 (1988); Vol. 57, p.18 (1977). http://orgsynth.org/orgsyn/pdfs/CV6P0468.pdf
  3. ^ Palladium- and copper-catalyzed cross-coupling and carbonylative cross-coupling of organotellurium compounds with organostannanes (Chem. Commun. 1999, 2117) - Royal Society of Chemistry Suk-Ku Kang, Sang-Woo Lee and Hyung-Chul Ryu Link
  4. ^ For an example see: Organic Syntheses, Coll. Vol. 9, p.234 (1998); Vol. 72, p.154 (1995). http://orgsynth.org/orgsyn/pdfs/CV9P0234.pdf