A Practical and Cost-Effective Method for the Synthesis of Bicyclo[2.2.2]octane-1,4-dicarboxylic Acid

Nicolas Le Marquer; Mathieu Yves Laurent; Arnaud Martel

doi:10.1055/s-0034-1380432

Synthesis, Table of Contents

Synthesis 2015; 47(15): 2185-2187
DOI: 10.1055/s-0034-1380432

psp

A Practical and Cost-Effective Method for the Synthesis of Bicyclo[2.2.2]octane-1,4-dicarboxylic Acid

Nicolas Le Marquer

Institut des Molécules et Matériaux du Mans, IMMM, UMR CNRS 6283, Université du Maine, 72085 Le Mans, France Email: arnaud.martel@univ-lemans.fr

,

Mathieu Yves Laurent

Institut des Molécules et Matériaux du Mans, IMMM, UMR CNRS 6283, Université du Maine, 72085 Le Mans, France Email: arnaud.martel@univ-lemans.fr

,

Arnaud Martel*

Institut des Molécules et Matériaux du Mans, IMMM, UMR CNRS 6283, Université du Maine, 72085 Le Mans, France Email: arnaud.martel@univ-lemans.fr

› Author Affiliations

Abstract

All articles of this category

Abstract

A short and efficient synthesis of bicyclo[2.2.2]octane-1,4-dicarboxylic acid involving the formation of a semicarbazone is developed, and a reproducible protocol for the reduction of this semicarbazone is described. The use of microwaves significantly shortens the duration of the sequence to the diacid compared to the previously described synthetic method. In addition, by shifting from the use of large amounts of Raney nickel to a solid-phase process, both the safety and cost are improved notably.

Key words

bicyclo[2.2.2]octane-1,4-dicarboxylic acid - safe - semicarbazone - microwave irradiation - rigid backbone - solid-phase

Full Text

References

References
1 Baker FW, Parish RC, Stock LM. J. Am. Chem. Soc. 1967; 89: 5677
2 Ermer O, Dunitz JD. Chem. Commun. 1968; 567
3 Goldsmith RH, Vura-Weis J, Scott AM, Borkar S, Sen A, Ratner MA, Wasielewski MR. J. Am. Chem. Soc. 2008; 130: 7659
4 Honegger E, Heilbronner E, Hess N, Martin HD. Chem. Ber. 1987; 120: 187
5 Kaszynski P, Januszko A, Ohta K, Nagamine T, Potaczek P, Young VG, Endo Y. Liq. Cryst. 2008; 35: 1169
6 Lemouchi C, Mézière C, Zorina L, Simonov S, Rodríguez-Fortea A, Canadell E, Wzietek P, Auban-Senzier P, Pasquier C, Giamarchi T, Garcia-Garibay MA, Batail P. J. Am. Chem. Soc. 2012; 134: 7880
7 Li K, Lee J, Olson DH, Emge TJ, Bi W, Eibling MJ, Li J. Chem. Commun. 2008; 6123
8 Liu Y, Turner SR. J. Polym. Sci., Part A: Polym. Chem. 2010; 48: 2162
9 Ritchie CD, Lewis ES. J. Am. Chem. Soc. 1962; 84: 591
10 Ritchie CD, Megerle GH. J. Am. Chem. Soc. 1967; 89: 1452
11 Taimr L, Smith JG. J. Polym. Sci., Part A: Polym. Chem. 1971; 9: 1203
12 Von Gersdorff J, Kirste B, Niethammer D, Harrer W, Kurreck H. Magn. Reson. Chem. 1988; 26: 416
13 Yuen T, Danilovic D, Li K, Li J. J. Appl. Phys. 2008; 103: 07B725
14 Roberts JD, Moreland WT. Jr, Frazer W. J. Am. Chem. Soc. 1953; 75: 637
15 Wang Y. CN101709034A, 2010
16 Holtz HD, Stock LM. J. Am. Chem. Soc. 1964; 86: 5183
17 Wood G, Woo EP. Can. J. Chem. 1968; 46: 3713

Supplementary Material

Supporting Information