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Updated: Jan 20, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes
James W Hilborn1, Reinaldo Moya-Barrios1, Alison Thompson1
1Department of Chemistry , Dalhousie University , P.O. Box 15000, Halifax , Nova Scotia B3H 4R2 , Canada.
Abstract:
The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction proceeds via intramolecular charge transfer from the donor to acceptor, thereby enhancing a pathway to produce, within the solvent cage, the desired diarylethane products. These in-cage naphthylarylethanes are produced in good yields, in a single photochemical step, with the use of cyclohexane as a solvent providing optimal yields.
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Nucleophilic Substitution
Nucleophilic substitution reactions are among the most fundamental topics covered in organic chemistry. A nucleophilic substitution reaction is one where a nucleophile (electron-rich Lewis base) replaces a leaving group from a carbon atom.
SN1 (S = Substitution, N = Nucleophilic, 1 = first-order kinetics)
SN2 (S = Substitution, N = Nucleophilic, 2 = second-order kinetics)
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Hydrolysis of an Ester
Triglycerides are triester molecules composed of a glycerol backbone that is bound to 3 fatty acids. These form the basis of many biological lipids that are found in vegetable oils and fats. Lipids that are isolated from plant material are the basis of vegetable oils, whereas lipids extracted from animals are used as lard or general sources of fats.
A fatty acid molecule has a long carbon chain — between 12 and 20 carbons — with a weak organic acid at one end. Some...
