{rfName}
Re

Indexed in

Altmetrics

Analysis of institutional authors

Melchiorre PAuthor

Share

April 27, 2020
Publications
>
Article
No

Reaction of dicarbonates with carboxylic acids catalyzed by weak Lewis acids: General method for the synthesis of anhydrides and esters

Publicated to: Synthesis-Stuttgart. (22): 3489-3496 - 2007-11-16 (22), DOI: 10.1055/s-2007-990812

Authors:

Bartoli G; Bosco M; Carlone A; Dalpozzo R; Marcantoni E; Melchiorre P; Sambri L
[+]

Affiliations

Alma Mater Studiorum Universita di Bologna - Author
Universita degli Studi di Camerino - Author
Universitá della Calabria - Author
See more

Abstract

The reaction between carboxylic acids (RCOOH) and dialkyl dicarbonates [(R1OCO)2O], in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol (R1OH) as the solvent, leads to the esters RCOOR1 in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride [(RCO)2O], R1OH and carbon dioxide. The esters arise from the attack of the alcohols on the anhydrides. Exploiting the lesser reactivity of tert-butyl alcohol in comparison with other alcohols, a clean synthesis of both carboxylic anhydrides and esters has been set up. In the former reaction, an acid/Boc2O molecular ratio of 2:1 leads to the anhydride in good to excellent yields, depending on the stability of the resulting anhydride to the usual workup conditions. In the latter reaction, stoichiometric mixtures of the acid and Boc2O are allowed to react with a twofold excess of a primary alcohol, secondary alcohol or phenol (R 2OH) to give the corresponding esters (RCOOR2). Purification of the products is particularly easy since all byproducts are volatile or water soluble. A very easy chromatography is required only in the case of nonvolatile alcohols. A broad variety of sensitive functional groups is tolerated on both the acid and the alcohol, in particular a high chemoselectivity is observed. In fact, no transesterification processes occur with the acid-sensitive acetoxy group and methyl esters. © Georg Thieme Verlag Stuttgart.
[+]

Keywords

AnhydridesEstersLewis acidsMagnesium saltsSynthetic methods

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Synthesis-Stuttgart due to its progression and the good impact it has achieved in recent years, according to the agency Scopus (SJR), it has become a reference in its field. In the year of publication of the work, 2007, it was in position , thus managing to position itself as a Q1 (Primer Cuartil), in the category Organic Chemistry.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2025-12-25:

  • Google Scholar: 65
  • WoS: 48
  • Scopus: 51
[+]

Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-12-25:

  • The use, from an academic perspective evidenced by the Altmetric agency indicator referring to aggregations made by the personal bibliographic manager Mendeley, gives us a total of: 99.
  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 99 (PlumX).

With a more dissemination-oriented intent and targeting more general audiences, we can observe other more global scores such as:

  • The Total Score from Altmetric: 13.
  • The number of mentions on the social network X (formerly Twitter): 1 (Altmetric).
[+]

Leadership analysis of institutional authors

This work has been carried out with international collaboration, specifically with researchers from: Italy.

[+]