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A Formal Rearrangement of Allylic Silanols

dc.contributor.authorDhokale, Ranjeet A.
dc.contributor.authorSeidl, Frederick J.
dc.contributor.authorSathyamoorthi, Shyam
dc.date.accessioned2021-12-08T21:49:54Z
dc.date.available2021-12-08T21:49:54Z
dc.date.issued2021-06-23
dc.identifier.citationDhokale, R.A.; Seidl, F.J.; Sathyamoorthi, S. A Formal Rearrangement of Allylic Silanols. Molecules 2021, 26, 3829. https://doi.org/10.3390/molecules26133829en_US
dc.identifier.urihttp://hdl.handle.net/1808/32274
dc.description.abstractWe 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.en_US
dc.publisherMDPIen_US
dc.rights© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.en_US
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en_US
dc.subjectRearrangementen_US
dc.subjectOrganic synthesisen_US
dc.subjectOrganic methodologyen_US
dc.titleA Formal Rearrangement of Allylic Silanolsen_US
dc.typeArticleen_US
kusw.kuauthorDhokale, Ranjeet A.
kusw.kuauthorSathyamoorthi, Shyam
kusw.kudepartmentMedicinal Chemistryen_US
dc.identifier.doi10.3390/molecules26133829en_US
dc.identifier.orcidhttps://orcid.org/ 0000-0002-3587-0191en_US
dc.identifier.orcidhttps://orcid.org/ 0000-0001-9327-4753en_US
dc.identifier.orcidhttps://orcid.org/ 0000-0003-4705-7349en_US
kusw.oaversionScholarly/refereed, publisher versionen_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.identifier.pmidPMC8270268en_US
dc.rights.accessrightsopenAccessen_US


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© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.
Except where otherwise noted, this item's license is described as: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.