Diels–Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid

Mohan Raj, Radhakrishnan ; Balasubramanian, Kalpattu K. ; Easwaramoorthy, Deivanayagam (2017) Diels–Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid Organic & Biomolecular Chemistry, 15 (5). pp. 1115-1121. ISSN 1477-0520

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Official URL: http://doi.org/10.1039/C6OB02006B

Related URL: http://dx.doi.org/10.1039/C6OB02006B

Abstract

This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids. The products were accomplished by the Diels–Alder cycloaddition reaction and their mechanistic pathways have been formulated. The impact of C2 and C2,5 substituents of the p-quinones on the cycloaddition reaction has been explored. Remarkably, it is the first report to explore this kind of in situ generated diene for the Diels–Alder cycloaddition reaction.

Item Type:Article
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ID Code:128966
Deposited On:07 Nov 2022 06:43
Last Modified:07 Nov 2022 06:43

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