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. 2019 Mar 15;84(6):3652-3655.
doi: 10.1021/acs.joc.8b03223. Epub 2019 Mar 6.

Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors

Jason V Chari  1 , Francesca M Ippoliti  1 , Neil K Garg  1
Affiliations

Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors

Jason V Chari et al. J Org Chem. .

Abstract

Silyl triflate precursors to cyclic alkynes and allenes serve as valuable synthetic building blocks. We report a concise and scalable synthetic approach to prepare the silyl triflate precursors to cyclohexyne and 1,2-cyclohexadiene. The strategy involves a retro-Brook rearrangement of an easily accessible cyclohexanone derivative, followed by triflation protocols. This simple, yet controlled, method should enable the further study of strained alkynes and allenes in chemical synthesis.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1.
Figure 1.
Strained cyclic alkynes and allenes.
Figure 2.
Figure 2.
Cycloadditions of cyclohexyne (2) and 1,2-cyclohexadiene (3).
Figure 3.
Figure 3.
Synthetic approaches to cyclohexyne precursors 20a and 20b and 1,2-cyclohexadiene precursors 21a and 21b.
Figure 4.
Figure 4.
Retro-Brook approach to silyl triflates 20b and 21b.
Figure 5.
Figure 5.
Examples of cycloadditions using silyl triflates 20b and 21b.
See this image and copyright information in PMC

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