Issue 13, 2021, Issue in Progress

Studies in the rearrangement reactions involving camphorquinone

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Nov 2020
Accepted
17 Jan 2021
First published
11 Feb 2021
This article is Open Access
Creative Commons BY license

RSC Adv., 2021,11, 7180-7186

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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