Shinohara, Riku published the artcileSN2 Reaction of Diarylmethyl Anions at Secondary Alkyl and Cycloalkyl Carbons, Name: 3-Pentanol, the main research area is alkyl diphenyl phosphate diarylmethyl anion nucleophilic substitution reaction; diarylmethyl substituted alkane preparation.
The substitution reaction of the di-Et allylic and propargylic phosphates with Ar2CH anions was applied to sec-alkyl phosphates to compare reactivity and stereoselectivity. However, the substitution took place on the Et carbon of the di-Et phosphate group. We then found that the di-Ph phosphate leaving group ((PhO)2PO2) was suited for the substitution at the sec-alkyl carbon. Enantioenriched di-Ph sec-alkyl phosphates with different substituents (Me, Et, iPr) on the vicinal position underwent the substitution reaction with almost complete inversion (>99% enantiospecificity). The substitution reactions of cyclohexyl phosphates possessing cis or trans substituents (Me and/or tBu) at the C4, C3, and C2 positions of the cyclohexane ring were also studied to observe the difference in reactivity among the cis and trans isomers. A transition-state model with the phosphate leaving group ((PhO)2PO2) in the axial position was proposed to explain the difference. This model was supported by computational calculation of the virtual substitution reaction of the structurally simpler “”dimethyl”” cyclohexyl phosphates (leaving group = (MeO)2PO2) with MeLi. Furthermore, the calculation unexpectedly indicated higher propensity of (PhO)2PO2 as a leaving reactivity than alkyl phosphate groups such as (MeO)2PO2 and (iPrO)2PO2.
European Journal of Organic Chemistry published new progress about Alkanes Role: SPN (Synthetic Preparation), PREP (Preparation) (aryl). 584-02-1 belongs to class alcohols-buliding-blocks, name is 3-Pentanol, and the molecular formula is C5H12O, Name: 3-Pentanol.
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