Publication

An unprecedented elimination-driven migration: the reductive dihalobornane-camphene rearrangement

Manfred Schlosser
1998
Journal Articles

Abstract

In the rearrangement of exo-2,10-dibromobornane to camphene it was demonstrated that even complex elimination processes which involve the breaking and making of several bonds can be brought about in a highly concerted fashion under variable push-pull control. Several trapping reactions, a failed radical reaction, and stereochem. studies were used to verify the mechanism. [on SciFinder (R)]

Official source

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Manfred Schlosser
1998
Journal Articles

Abstract

Official source

Related concepts (3)

Rearrangement reaction

In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular. In the example below, the substituent R moves from carbon atom 1 to carbon atom 2: Intermolecular rearrangements also take place.

Claisen rearrangement

The Claisen rearrangement is a powerful carbon–carbon bond-forming chemical reaction discovered by Rainer Ludwig Claisen. The heating of an allyl vinyl ether will initiate a [3,3]-sigmatropic rearrangement to give a γ,δ-unsaturated carbonyl, driven by exergonically favored carbonyl CO bond formation (ΔΔHf = -327 kcal·mol−1). The Claisen rearrangement is an exothermic, concerted (bond cleavage and recombination) pericyclic reaction. Woodward–Hoffmann rules show a suprafacial, stereospecific reaction pathway.

Elimination reaction

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists.