Little work has been done with 1,2,3-cyclohexatrienes previously which made it an interesting target for its broader evaluation as a reagent. credit: nature (2023). DOI: 10.1038/s41586-023-06075-8
A team of chemists at the University of California, Los Angeles has found that the benzene isomer 1,2,3-cyclohexatrine has the potential to be a versatile reagent in organic synthesis. In their study, reported in the journal natureAndrew Keligan, Anna Bolger, Dominic Witkowski and Neil Garg experimented with the high-energy compound.
For many years, 1,2,3-cyclohexatrine was virtually ignored as a useful reagent for use in organic synthesis – it was considered too unstable to be used. However, it is promising because it is higher in energy than gasoline.
Also, isomers of benzene in general have long been of interest to organic chemists due to their ability to synthesize useful organic substances. In this new effort, the researchers believed that, under the right conditions, the isomer 1,2,3-cyclohexatrine could be useful as a reagent for the production of a wide variety of organic compounds.
The team first began producing samples using a method developed in the 1990s to generate intermediates from precursors. They then used a variety of techniques to produce a set of close rings, all of which likely interact well, like benzene, with core fans. They then set to work with the resulting material to determine whether it could be used as an effective reagent.
To test its potential as an electrophilic reagent, the team performed a set of trapping reactions with dimethyl tertiary. Then also use members of the sily1 group to show how nucleophilic interactions can take place and also perform interactions that show the possibility of introducing σ bonds. The group also performed computational studies in combination with experimental analysis which showed that 1,2,3-cyclohexatrine derivatives can be used in certain reactions despite their high reactivity and limited lifetime.
The team also showed that 1,2,3-cyclohextrin can be used in synthetic sequences that include many steps, which, they note, shows its usefulness in building chemically complex molecules both sterically and topologically. They concluded that such isomers and their derivatives deserve further research for their use in creating organic materials.
more information:
Andrew V. Keligan et al., Strain Promoter Interactions of 1,2,3-Cyclohexatrine and Derivatives, nature (2023). DOI: 10.1038/s41586-023-06075-8
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the quote: New Look at 1,2,3-Cyclohexatrine Shows It Can Be Used as a Versatile Reagent in Organic Synthesis (2023, May 3) Retrieved May 3, 2023 from https://phys.org/news/2023-05-fresh- cyclohexatriene- a versatile reagent- synthesis.html
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