Publication

2-Ethoxyvinyllithiums and diethoxyvinyllithiums: what makes them stable or fragile?

Manfred Schlosser
1997
Journal Articles

Abstract

The elusive (E)-2-ethoxyvinyllithium can be readily generated in THF at -75 Deg from (E)-1-bromo-2-ethoxyethylene by halogen/metal exchange and subsequently trapped with electrophiles. Alkylation opens a convenient entry to (E)-configurated enethers. (E)-2-Ethoxyvinyllithium decomps. rapidly at -50 Deg whereas its (Z)-isomer, which lacks the possibility to eliminate LiOEt in a favorable antiperiplanar process, is stable under the same conditions. (E)-1,2-Diethoxyvinyllithium even sustains reflux temps. (.apprx.75 Deg). 2,2-Diethoxyvinyllithium and (Z)-1,2-diethoxyvinyllithium can be conserved at 0 Deg although this time loss of alcoholate can occur in the anti-mode. Obviously it matters whether the energy-rich ethoxyacetylene is formed as the elimination product or simple acetylene, as in the case of (E)-2-ethoxyvinyllithium. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/a441f436-8299-4e6c-bf48-9ba085064a44

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Manfred Schlosser
1997
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/a441f436-8299-4e6c-bf48-9ba085064a44

About this result

Related concepts (32)

Metal–halogen exchange

In organometallic chemistry, metal–halogen exchange is a fundamental reaction that converts an organic halide into an organometallic product. The reaction commonly involves the use of electropositive metals (Li, Na, Mg) and organochlorides, bromides, and iodides. Particularly well-developed is the use of metal–halogen exchange for the preparation of organolithium compounds. Two kinds of lithium–halogen exchange can be considered: reactions involving organolithium compounds and reactions involving lithium metal.

Electrophile

In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through addition and substitution reactions.

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Related publications (1)

2-Ethoxyvinyllithiums and diethoxyvinyllithiums: what makes them stable or fragile?

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Catalytic hydrogenation by triruthenium clusters: A mechanistic study with parahydrogen-induced polarization