In 1983 was firstly described the Barton decarboxylation.[1] Since then, numerous papers described not only the use of this reaction, but also its mechanistic aspects and although green chemistry is becoming a major issue,[2] Barton decarboxylation has never been studied in aqueous media. This has many advantages over usual organic solvents: it is the least expensive and safest solvent that is non-flammable, inexplosive and nontoxic. However, the major problem encountered by organic chemists is the low solubility of their reactants in water. To overcome this problem, different strategies have been studied: the use of organic co-solvents as well as additives such as phase transfer agents, or surfactants.[3] In this presentation will be discussed a Barton-like radical decarboxylation reaction in micellar media, and its improvement by sonication. Moreover, the bio-availability of fatty acids allows the eco-friendly formation of new surfactants, symmetric or not, by even and odd homologation. Among the various compounds possibilities will be discussed the physicochemical properties of the Gemini surfactant obtained. [1] D.H.R. Barton, D. Crich, W.B. Motherwell J. Chem. Soc., Chem. Commun. 1983, 939-941. [2] P.T. Anastas, J.C.W. Green Chemistry, Theory and Practice Oxford University Press, Oxford (1998). [3] see for example M. Billamboz, F. Mangin, N. Drillaud, C. Chevrin-Villette, E. Banaszak-Léonard, C. Len J. Org. Chem. 2014, 79, 493-500.

Radical decarboxylation in micellar media for the formulation of new surfactants

249th National Meeting (2015)

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