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Issue 5, 2017
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Diels–Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid

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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.

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

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Supplementary files

Article information


Submitted
12 Sep 2016
Accepted
05 Jan 2017
First published
05 Jan 2017

Org. Biomol. Chem., 2017,15, 1115-1121
Article type
Communication

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

R. Mohan Raj, K. K. Balasubramanian and D. Easwaramoorthy, Org. Biomol. Chem., 2017, 15, 1115
DOI: 10.1039/C6OB02006B

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