Publication

Metalation of Pyrans and Dihydropyridines : When is an 8pi-System Cost Effective ?

Manfred Schlosser
1979
Journal Articles

Abstract

The pyrans I (R = Me, H; R1 = H) with BuLi/KOCMe3 or KSiMe3 gave the 2-metalated derivs. I (R1 = K), which reacted with alkyl halides to give I (R = H, Me; R1 = Me, Et, SiMe3, CH2SiMe3); thus the behavior the 4H-pyrans toward organometallic reagents is similar to that of 3,4-dihydro-2H-pyrans. The pyridine II (R2 = Me, R3 = H) was metalated with BuLi/KOCMe3 only in the 2-position to give II (R3 = H), whereas the metalation position of II (R2 = R3 = H) depends on the reagent; thus, II (R2 = R3 = H) reacted with BuLi/KOCMe3 and MeI to give II (R2 = H, R3 = Me), whereas with KSiMe3 in THF and MeO gave a 1:1 mixt. of II (R2 = H, R3 = Me) and II (R2 = Me, R3 = H). This is the first example of proton removal from the allylic position of a dihydropyridine to form an organometallic 8p system. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/48ce26a7-44d3-4bfe-8063-210ad4cbb613

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Manfred Schlosser
1979
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/48ce26a7-44d3-4bfe-8063-210ad4cbb613

About this result

Related concepts (18)

Organometallic chemistry

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well.

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.

Group 2 organometallic chemistry

Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organmetallic group 2 compounds are rare and are typically limited to academic interests. As the group 2 elements (also referred to as the alkaline earth metals) contain two valence electrons, their chemistries have similarities group 12 organometallic compounds.

Related publications (2)

Metalation of Pyrans and Dihydropyridines : When is an 8pi-System Cost Effective ?

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