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    The neighbouring effect of isosorbide and its epimers in their reactions with dimethyl carbonate

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        Abstract

        The reactions of isosorbide and its epimers, isomannide and isoidide, with dimethyl carbonate have been herein investigated as easy access to bio-based products by a free-halogen chemistry approach. Isosorbide and its epimers show a different reactivity in bimolecular nucleophilic substitution with dimethyl carbonate (DMC). Carboxymethylation reaction was carried out in the presence of DMC and a weak base resulting in the high-yielding synthesis of dicarboxymethyl derivatives. Isomannide was the most reactive anhydro sugar due to the less sterically hindered exo position of the OH groups. On the other hand, methylation of isosorbide and its epimers, conducted in the presence of a strong base and DMC, showed the higher reactivity of the endo hydroxyl group, isoidide being the most reactive epimer. This result has been ascribed to the neighboring effect due to the combination of the oxygen in β-position and the intramolecular hydrogen bond within the anhydro sugar structure. Methylation reactions were also conducted in autoclave at high temperature with the amphoteric catalyst hydrotalcite using DMC as reagent and solvent. In this case, the reactivity of the epimers resulted quite differently with isosorbide being the most reactive reagent possibly as a result of the structure of hydrotalcite comprising of both acidic and basic sites. The neighboring effect was observed with good evidence in these methylation reactions.

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        Most cited references 42

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              Author and article information

              Affiliations
              [1 ]Dipartimento Scienze Ambientali, Informatica e Statistica, Università Ca' Foscari di Venezia, Dorsoduro 2137, 30123, Venice, Italy
              Author notes
              [* ]Corresponding author's e-mail address: tundop@ 123456unive.it
              Contributors
              Journal
              SOR-CHEM
              ScienceOpen Research
              ScienceOpen
              2199-1006
              20 October 2014
              16 March 2016
              : 0 (ID: febec666-00fe-4463-9a7b-91cc0ee0bcab )
              : 0
              : 1-11
              3601:XE
              10.14293/S2199-1006.1.SOR-CHEM.AB3R7E.v2
              © 2014 F. Aricò et al.

              This work has been published open access under Creative Commons Attribution License CC BY 4.0 , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Conditions, terms of use and publishing policy can be found at www.scienceopen.com .

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              Figures: 8, Tables: 6, References: 65, Pages: 11
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