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Issue 13, 2021, Issue in Progress
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Studies in the rearrangement reactions involving camphorquinone

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Abstract

Skeletal rearrangements of camphor are well-known, however, those involving camphorquinone, its sibling, are rare. We have found that the diol derived from allylated camphorquinone undergoes iodine or bromine mediated deep-seated skeletal rearrangement to provide an interesting tricyclic ring system. The iodo group in the rearranged product provided convenient leverage for further functionalization. For example, it was converted into an azide and the azide was subjected to copper(I) mediated Huisgen 1,3-dipolar cycloaddition with acetylenes to obtain a terpene–triazole conjugate.

Graphical abstract: Studies in the rearrangement reactions involving camphorquinone

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Supplementary files

Article information


Submitted
19 Nov 2020
Accepted
17 Jan 2021
First published
11 Feb 2021

This article is Open Access

RSC Adv., 2021,11, 7180-7186
Article type
Paper

Studies in the rearrangement reactions involving camphorquinone

H. S. P. Rao, A. Saha and S. Vijjapu, RSC Adv., 2021, 11, 7180
DOI: 10.1039/D0RA09839F

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