Related Experiment Video
Updated: Mar 7, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
CAr-O Rotamers in 3,3'-Disubstituted BINOL Esters
Takeo Sakai1, Junpei Matsuoka1, Masayuki Shintai1
1Faculty of Pharmacy, Meijo University , 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan.
Abstract:
Rotamers around the CAr-O bond were disclosed in 3,3'-disubstituted BINOL esters by NMR spectroscopy. A bulky R1 group increased the rotational barrier. The pivalate showed two rotamers at 2 °C, and broad signals were observed close to room temperature when R2 = Ph. The highest rotational barrier was recorded for the (tetracyanocyclopentadienyl)carboxylate, and C-O rotamers were present at room temperature. DFT calculations indicated the presence of repulsion between R1 and R2 during rotation of the CAr-O bond.
More Related Videos
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis