Georg Wittig – discovered witting rearrangement prepared phenyllithium

Georg Wittig – discoverer of witting rearrangement

Category : Personalities
Published by : Data Research Analyst, Worldofchemicals.com

Biography & contributions

Georg Wittig, a German chemist and Nobel laureate born on June 16, 1897 – died on August 26, 1987. Wittig’s well known discovery in the field of chemistry was witting rearrangement reaction and dehydrobenzol chemical compound.

He was awarded with various medals and awards such as silver medal from the university of Helsinki in the year of 1957, Dannie Heinemann award from the Gottingen academy of sciences in the year of 1965, Otto Hahn award for chemistry and physics in the year of 1967, Paul Karrer medal from the university of zurich in the year of 1972, Nobel Prize in organic phosphorus compounds work in the year of 1979,.

Wittig did research on the subject of ring tension and double bonds as well as valency tautomerism. One of his main research topics was the organic reactions of alkali metals and elaboration of carbon-based chemistry. He discovered the halogen metal exchange reaction.

Witting rearrangement

It is of two types

  • 1,2-Wittig rearrangement
  • [2,3]-Wittig rearrangement

1,2-Wittig rearrangement

A 1,2-Wittig rearrangement is a categorization of chemical reactions in organic chemistry, and consists of a 1,2-rearrangement of an ether with an alkyllithium compound. The intermediate product is an alkoxy lithium salt and the final product an alcohol. When R2 is a good leaving group and electron withdrawing functional group such as a cyanide (CN) group, this group is eliminated and the corresponding ketone is formed.

2,3-Wittig rearrangement

The [2,3]-Wittig rearrangement is the transformation of an allylic ether into a homoallylic alcohol via a concerted, pericyclic process. The mechanism of the 2,3-wittg rearrangement is a concerted thermally allowed sigmatropic reaction which follows the Woodward-Hoffman rules and proceeds through a six-electron, five membered transition state in a supra facial fashion. The reactions are usually carried out at a low temperature in order to prevent the competing Wittig 1,2-rearrangement.

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