Creary, Xavier published the artcileγ-Trimethylsilylcyclobutyl Carbocation Stabilization, COA of Formula: C5H10O, the publication is Journal of Organic Chemistry (2015), 80(3), 1781-1788, database is CAplus and MEDLINE.
Isomeric 3-trimethylsilyl-1-arylcyclobutyl carbocations, where the cross-ring 3-trimethylsilyl group has the potential to interact with the cationic center, were generated under solvolytic conditions. When the cationic center can interact with the rear lobe of the carbon-silicon bond, rate enhancements become progressively larger as the substituent on the aryl group becomes more electron-withdrawing. When the potential interaction with the trimethylsilyl group is via a front lobe interaction, there is minimal rate enhancement over the range of substituents. Computational studies also were carried out on these cations. Calculated trimethylsilyl stabilization energies progressively increase with electron-withdrawing character of the aryl groups when the trimethylsilyl interaction is via the rear lobe. But there are minimal changes in stabilization energies when the potential trimethylsilyl interaction is via the front lobe of the carbon-silicon bond. These computational studies, along with the solvolytic studies, point to a significant rear lobe 3-trimethylsilyl stabilization of arylcyclobutyl cations. They also argue against any front lobe stabilization of the isomeric arylcyclobutyl cations.
Journal of Organic Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, COA of Formula: C5H10O.
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