Ring Strain-promoted Allylic Transposition of Cyclic Silyl Ethers
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Chemistry
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Relief of the ring strain of medium-sized rings promotes a regioselective allylic transposition of a C-O bond when catalyzed by rhenium oxide. Through the allylic transposition, eight-membered cyclic silyl ethers undergo ring contraction to the corresponding six-membered siloxacycles.
Liu J, Chen M Chem Sci. 2023; 14(30):8103-8108.
PMID: 37538826 PMC: 10395275. DOI: 10.1039/d2sc07059f.
A Formal Rearrangement of Allylic Silanols.
Dhokale R, Seidl F, Sathyamoorthi S Molecules. 2021; 26(13).
PMID: 34201779 PMC: 8270268. DOI: 10.3390/molecules26133829.
Anderson T, Woerpel K Org Lett. 2020; 22(14):5690-5694.
PMID: 32643945 PMC: 7368818. DOI: 10.1021/acs.orglett.0c02075.
Vyvyan J, Engles C, Bray S, Wold E, Porter C, Konev M Beilstein J Org Chem. 2017; 13:2122-2127.
PMID: 29062432 PMC: 5647712. DOI: 10.3762/bjoc.13.209.
Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles.
Sittiwong W, Richardson M, Schiaffo C, Fisher T, Dussault P Beilstein J Org Chem. 2013; 9:1526-32.
PMID: 23946852 PMC: 3740507. DOI: 10.3762/bjoc.9.174.