Diels-Alder

Diene plus dienophile

A Diels-Alder reaction is a chemical reaction in which a diene (a molecule with two double bonds) combines with a dienophile (a molecule with one double bond) to form a six-membered ring.

The reaction is fundamental to organic chemistry, used to build complex molecules efficiently: The Diels-Alder reaction created the ring structure needed for the synthesis.

Named after the German chemists who discovered it in 1928.

historical

Nobel Prize

Highest academic honor

landmark · classic · textbook · Woodward · Hoffmann · organic chemistry · pioneering · milestone

mechanism

diene

Two C=C bonds present

  • concertedJointly arranged or carried out
  • endoPrefix meaning inside
  • exoPrefix for outer

synchronous · six-membered ring · electron flow · thermal · allowed

substrates

butadiene

Conjugated four-carbon diene

quinone · isoprene · conjugated · activated · substituted

synthesis

natural products

Compounds from organisms

scaffold · terpenes · alkaloids · steroids · pharmaceutical · drug discovery · methodology · strategy · disconnection

selectivity

ortho

Right-angled prefix

  • metaSelf-aware or transcendent
  • paraMilitary skydiver, briefly
  • asymmetricNot identical on both sides

chiral auxiliary · kinetic · thermodynamic · catalyst

variants

intramolecular

Within a single molecule

photochemical · high-pressure · aqueous · enzymatic

Categories
Opposites
reaction mechanism type

Diels-AlderSN2 reaction

Second-order nucleophilic displacement

molecular complexity change

Diels-Alderfragmentation

Breaking into smaller pieces

depolymerization

Familiarity
Top 1,000,000
Profile
Used worldwide · Timeless · Abstract · Rated G