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Thermodynamic vs. kinetic control in the Diels-Alder cycloaddition of cyclopentadiene to 2,3-dicyano-p-benzoquinone: Kinetic control revisited

✍ Scribed by Alan P. Marchand; Bishwajit Ganguly; William H. Watson; Satish G. Bodige

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 318 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00662-0

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✦ Synopsis

Diels-Alder cycloaddition of cyclopentadiene (1) to 2,3-dicyano-p-benzoquinone (2), when performed in methanol solvent at ambient temperature (kinetic control), gave 3b. Reduction of 3b, carried out under mild conditions by using CeCI3-NaBH4, proceeded stereospecifically to afford diol $. Subsequently, $ was converted into the corresponding bis(O-acetyl) derivative, 6, whose structure was established unequivocally via application of X-ray crystallographic methods. An earlier suggestion that 3a results via kinetic control of Diels-Alder cycloaddition of I to 2 is thereby shown to be erroneous.

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