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A Formal Rearrangement of Allylic Silanols
Dhokale, Ranjeet A. Seidl, Frederick J. Sathyamoorthi, Shyam
Dhokale, Ranjeet A.
Seidl, Frederick J.
Sathyamoorthi, Shyam
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Abstract
We show that 1M aqueous HCl/THF or NaBH4/DMF allows for demercurative ring-opening of cyclic organomercurial synthons into secondary silanol products bearing terminal alkenes. We had previously demonstrated that primary allylic silanols are readily transformed into cyclic organomercurials using Hg(OTf)2/NaHCO3 in THF. Overall, this amounts to a facile two-step protocol for the rearrangement of primary allylic silanol substrates. Computational investigations suggest that this rearrangement is under thermodynamic control and that the di-tert-butylsilanol protecting group is essential for product selectivity.
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2021-06-23
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MDPI
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Dhokale_2021.pdf
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Keywords
Rearrangement, Organic synthesis, Organic methodology
Citation
Dhokale, R.A.; Seidl, F.J.; Sathyamoorthi, S. A Formal Rearrangement of Allylic Silanols. Molecules 2021, 26, 3829. https://doi.org/10.3390/molecules26133829