Publication

1,2-elimination of alcohol from homoallyl ethers under the influence of mixed metal bases

Manfred Schlosser
1990
Journal Articles

Abstract

Lithium diisopropylamide in the presence of catalytic amts. of potassium tert-butoxide smoothly converts homoallyl or homobenzyl type ethers to dienes or styrenes. g,d-Unsatd. acetals give 1,3-dienyl ethers and 4-alkylidenetetrahydropyrans or dihydropyrans produce a variety of dienols. If there is a choice, the new double bond is formed with high trans selectivity while the configuration of existing double bonds is retained. The elimination mode is syn-periplanar and concerted, though E1cb like. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/d5dc24a8-5863-4448-ae22-a15e8e08a332

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Manfred Schlosser
1990
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/d5dc24a8-5863-4448-ae22-a15e8e08a332

About this result

Related concepts (17)

Double bond

In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O).

Organoboron chemistry

Organoboron chemistry or organoborane chemistry is the chemistry of organoboron compounds or organoboranes, which are chemical compounds of boron and carbon that are organic derivatives of borane (BH3), for example trialkyl boranes. . Organoboron compounds are important reagents in organic chemistry enabling many chemical transformations, the most important ones being hydroboration and carboboration. Reactions of organoborates and boranes involve the transfer of a nucleophilic group attached to boron to an electrophilic center either inter- or intramolecularly.

Bent bond

In organic chemistry, a bent bond, also known as a banana bond, is a type of covalent chemical bond with a geometry somewhat reminiscent of a banana. The term itself is a general representation of electron density or configuration resembling a similar "bent" structure within small ring molecules, such as cyclopropane (C3H6) or as a representation of double or triple bonds within a compound that is an alternative to the sigma and pi bond model.

Related publications (1)

1,2-elimination of alcohol from homoallyl ethers under the influence of mixed metal bases

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