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Asymmetric Diels-Alder reaction is one step in the biosynthesis of the statin lovastatin. [60] The retro-Diels–Alder reaction is used in the industrial production of cyclopentadiene. Cyclopentadiene is a precursor to various norbornenes, which are common monomers. The Diels–Alder reaction is also employed in the production of vitamin B6.
Some examples of this are shown in schemes 5 and 8, in an ester exchange, and disulfide exchange reactions. The second type, formation reactions, rely on the formation of new covalent bonds. Some examples include Diels–Alder and aldol reactions. In some cases, a reaction can pertain to both categories.
The synchronous 6π-electron Diels-Alder reaction is a [π 4 s + π 2 s]-cycloaddition (i.e. suprafacial with respect to both components), as exemplified by the reaction to the right. The Diels-Alder reaction is suprafacial with respect to both components. Thus as the total number of antarafacial components is 0, which is even, the reaction is ...
PTAD is one of the strongest dienophiles and reacts rapidly with dienes in Diels-Alder reactions. [1] The most prominent use of PTAD was the first synthesis of prismane in 1973. [ 2 ]
The aza-Diels–Alder reaction is a modification of the Diels–Alder reaction wherein a nitrogen replaces sp 2 carbon. [1] The nitrogen atom can be part of the diene or the dienophile . The Aza Diels–Alder reaction, general scope
Depending on the substrate chosen, the HDDA reaction can be initiated thermally or by the addition of a suitable catalyst, often a transition metal. [1] [2] [4] [5] The prevailing mechanism for the thermally-initiated HDDA reaction is a [4+2] cycloaddition between a conjugated diyne (1,3-dialkyne) and an alkyne (often referred to as a diynophile in analogy to the Diels–Alder dienophile) to ...
English: Comparison between Diels-Alder reaction of cyclopentadiene with 2-methylthioacrylonitrile and captodative-enhanced Friedel-Crafts reaction of benzene with 1-nitrovinyl alcohol Date 11 October 2017
Norbornene is made by a Diels–Alder reaction of cyclopentadiene and ethylene.Many substituted norbornenes can be prepared similarly. [2] [3] Related bicyclic compounds are norbornadiene, which has the same carbon skeleton but with two double bonds, and norbornane which is prepared by hydrogenation of norbornene.