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The retro-Diels–Alder reaction (rDA reaction) is the reverse of the Diels–Alder (DA) reaction, a [4+2] cycloelimination. It involves the formation of a diene and dienophile from a cyclohexene . It can be accomplished spontaneously with heat, or with acid or base mediation.
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 Diels-Alder reaction is perhaps the most important and commonly taught cycloaddition reaction. Formally it is a [4+2] cycloaddition reaction and exists in a huge range of forms, including the inverse electron-demand Diels–Alder reaction, hexadehydro Diels–Alder reaction and the related alkyne trimerisation.
[1] [2] Mass spectra is a plot of relative abundance against mass-to-charge ratio. It is commonly used for the identification of organic compounds from electron ionization mass spectrometry. [3] [4] Organic chemists obtain mass spectra of chemical compounds as part of structure elucidation and the analysis is part of many organic chemistry ...
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.
P 2 has been suggested to form as an intermediate in the photolysis of P 4, [5] and in the presence of 2,3-dimethyl-1,3-butadiene the diphosphane resulting from Diels–Alder addition is again formed. [6] To date, no direct evidence of P 2 formation via P 4 photolysis exists.
In the history of the Nobel Prize in Chemistry awards have been given for the invention of specific organic reactions such as the Grignard reaction in 1912, the Diels–Alder reaction in 1950, the Wittig reaction in 1979 and olefin metathesis in 2005.
Diels-Alder reaction and inverse electron demand Diels-Alder reaction [9] [10] [4+1] cycloadditions between isonitriles (isocyanides) and tetrazines [11] nucleophilic substitution especially to small strained rings like epoxy [12] and aziridines; carbonyl-chemistry-like formation of ureas but not reactions of the aldol type due to low ...
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