Reaccion-de-Diels-Alder
Reminder: These notes are meant to supplement, not replace, the laboratory manual.
A Diels-Alder Reaction
History and Application: The 1950 Nobel prize in chemistry was awarded to Otto Paul Hermann Diels and Kurt Alder for their breakthrough work on the discovery and development of [4 + 2] cycloaddition reactions i. This set of reactions are enormously useful in the synthesis of six membered rings in a single stepii. These are used in many pharmaceutical applications. Tamiflu® is a drug which shortens the duration of flu symptomsiii. Tamiflu is the most widely oral anti-influenza product in the US. iv
Diene Dienophile
Diels-Alder Adduct
Tamiflu®
A third generation synthesis of Tamiflu was achieved in 12 steps from commercially available starting materials, using the Diels–Alder reaction and Curtius rearrangement as key steps.v1 Many other important drugs utilize a Diels-Alder reaction step in their synthesis. Safety considerations for this experiment include: All of the compounds involved in this experiment are at least slightly toxic, and all four of the solvents are highly flammable. Handle them with the usual precautions. You will be using a sand bath and a Mel-Temp apparatus during this experiment. As you know by now, portions of both of these pieces of equipment become very hot during normal use. Handle them with care, and don't touch the hot parts. They also use electricity; do not use water or other solvents carelessly around them. If the wires on any electrical apparatus are frayed, the shock and fire hazards are multiplied; do not use the apparatus. Terminology Pericyclic Reactions: Any one of a number of reactions which proceed 1) in a concerted fashion, 2) the electrons move around a closed loop, and has a 3) cyclic transition state. Members of this group of reactions include cycloaddition reaction
reactions of which the [4 +2] Diels-Alder is a member, electrocyclic reactions and sigmatropic rearrangements. vi Cycloaddition Reaction-
A Diels-Alder Reaction
History and Application: The 1950 Nobel prize in chemistry was awarded to Otto Paul Hermann Diels and Kurt Alder for their breakthrough work on the discovery and development of [4 + 2] cycloaddition reactions i. This set of reactions are enormously useful in the synthesis of six membered rings in a single stepii. These are used in many pharmaceutical applications. Tamiflu® is a drug which shortens the duration of flu symptomsiii. Tamiflu is the most widely oral anti-influenza product in the US. iv
Diene Dienophile
Diels-Alder Adduct
Tamiflu®
A third generation synthesis of Tamiflu was achieved in 12 steps from commercially available starting materials, using the Diels–Alder reaction and Curtius rearrangement as key steps.v1 Many other important drugs utilize a Diels-Alder reaction step in their synthesis. Safety considerations for this experiment include: All of the compounds involved in this experiment are at least slightly toxic, and all four of the solvents are highly flammable. Handle them with the usual precautions. You will be using a sand bath and a Mel-Temp apparatus during this experiment. As you know by now, portions of both of these pieces of equipment become very hot during normal use. Handle them with care, and don't touch the hot parts. They also use electricity; do not use water or other solvents carelessly around them. If the wires on any electrical apparatus are frayed, the shock and fire hazards are multiplied; do not use the apparatus. Terminology Pericyclic Reactions: Any one of a number of reactions which proceed 1) in a concerted fashion, 2) the electrons move around a closed loop, and has a 3) cyclic transition state. Members of this group of reactions include cycloaddition reaction
reactions of which the [4 +2] Diels-Alder is a member, electrocyclic reactions and sigmatropic rearrangements. vi Cycloaddition Reaction-