Homoallylboration of Aldehydes: Stereoselective Synthesis of Allylic-Substituted Alkenes and E-Alkenes was written by Polyak, Daniel;Xu, Bokai;Krauss, Isaac J.. And the article was included in Organic Letters in 2022.HPLC of Formula: 105-13-5 This article mentions the following:
In this study, the scope and reactivity of homoallylation with cyclopropylcarbinylboronates I (R = Et, but-3-en-1-yl, Ph, Bn, etc.) bearing various aliphatic and aromatic 浼? and 绾?substituents were explored. The 浼?alkyl substituted boronates I afforded E-disubstituted alkenyl secondary alcs. C6H5CH2CH2CH(OH)CH2CH2CH=CHR in high e.r., while aryl substituents promoted rearrangement. The 绾?alkyl substituents all resulted in diastereoselective homoallylation, while aryl substitution changed the outcome to cyclopropylcarbinylation. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5HPLC of Formula: 105-13-5).
(4-Methoxyphenyl)methanol (cas: 105-13-5) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).HPLC of Formula: 105-13-5
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem