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Ti-catalyzed reaction of β-pinene with BF3·THF
Published: 14 November 2022 by MDPI in The 26th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
The reaction of β-pinene with BF3·THF in the presence of the catalytic system Cp2TiCl2/Mg was carried out for the first time to obtain a previously undescribed 1-fluoro-substituted boraspirane. The reaction proceeds stereoselectively, but is complicated by the rearrangement of the β-pinene under the Ti-catalyzed reaction conditions.
Keywords: cycloboration; organoborane compounds, β-pinene, Cp2TiCl2.
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Comments on this paper
18 November 2022
This reminds me of the Kulinkovich reaction, except it's adapted to work with boron. So the product boriranes will be strained, like epoxides, but have partial negative charge on carbon. It's sort of an anti-epoxide -- a strained nucleophile instead of a strained electrophile. I look forward to seeing how boriranes react with carbonyl compounds or epoxides and what can be made from those products!