The Chemistry of Dienes and Polyenes | Wiley Online Books
Cited By. This article is cited by 65 publications. Pd-Catalyzed Stereoselective 1,2-Aryboration of Alkenylarenes. Organic Letters , 21 17 , DOI: Journal of the American Chemical Society , 35 , Organic Letters , 21 15 , Organic Letters , 21 12 , Journal of the American Chemical Society , 18 , Dhungana, Bijay Shrestha, Timothy J. Boyle, Ramesh Giri. Journal of the American Chemical Society , 46 , Organic Letters , 20 19 , Journal of the American Chemical Society , 39 , Kevin Brown. Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes.
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The catalyst is derived from Re 2 O 7 on alumina. The most heavily practiced reaction of alkenes, dienes included, is polymerization. Chloroprene is related but it is a synthetic monomer. An important reaction for conjugated dienes is the Diels—Alder reaction. Many specialized dienes have been developed to exploit this reactivity for the synthesis of natural products e.
The Chemistry of Dienes and Polyenes
Conjugated dienes add reagents such as bromine and hydrogen by both 1,2-addition and 1,4-addition pathways. Addition of polar reagents can generate complex architectures: . Nonconjugated dienes are substrates for ring-closing metathesis reactions. These reactions require a metal catalyst :.
The position adjacent to a double bond is acidic because the resulting allyl anion is stabilized by resonance. This effect becomes more pronounced as more alkenes are involved to create greater stability. For example, deprotonation at position 3 of a 1,4-diene or position 5 of a 1,3-diene give a pentadienyl anion. An even greater effect is seen if the anion is aromatic, for example, deprotonation of cyclopentadiene to give the cyclopentadienyl anion. Dienes are widely used chelating ligands in organometallic chemistry.
In some cases they serve as placeholder ligands, being removed during a catalytic cycle. For example, the cyclooctadiene "cod" ligands in bis cyclooctadiene nickel 0 are labile. In some cases, dienes are spectator ligands, remaining coordinated throughout a catalytic cycle and influencing the product distributions.
Chiral dienes have also been described. From Wikipedia, the free encyclopedia. This article is about organic chemicals. For the surname "Diene" used in West Africa, see Serer people. Noels Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. Organic Syntheses.