No.118
Methanesulfonic Acid Esters
| M1446 | Methanesulfonic Acid 2-Methoxyethyl Ester (1) |
25g |
| M1193 | Methanesulfonic Acid 2,2,2-Trifluoroethyl Ester (2) |
5g |
The electron density of α-carbon atom in methanesulfonic acid esters is lowered by the influence of the sulfonyloxy group. Consequently, methanesulfonic acid esters are attacked by nucleophilic reagents to proceed a substitution reaction at the α-carbon smoothly.
Methanesulfonic acid esters 1 and 2 are used as functional ethylation agents. For example, the indene derivative prepared by reaction of 1 with indenyllithium can serve as a ligand of catalyst 3, which can be useful in polymerization of styrenes, etc.1,2) In addition, 2 can be utilized for the synthesis of fluorine-containing ether compounds.3)
References
1) Chiral lanthanocene complexes with an ether-functionalized
indene ligand
C. Qian, G. Zou, J. Sun, J. Organomet. Chem., 566, 21 (1998).
2) The synthesis and polymerization behavior of methoxy-
substituted (indenyl)trichlorotitanium complexes
P. Foster, M. D. Rausch, J. C. W. Chien, J. Organomet. Chem., 527, 71 (1997).
3) A simple method for preparation of aryl 2,2,2-trifluoroethyl ethers
F. Camps, J. Coll, A. Messeguer, M. A. Pericas, Synthesis, 1980, 727.
indene ligand
C. Qian, G. Zou, J. Sun, J. Organomet. Chem., 566, 21 (1998).
2) The synthesis and polymerization behavior of methoxy-
substituted (indenyl)trichlorotitanium complexes
P. Foster, M. D. Rausch, J. C. W. Chien, J. Organomet. Chem., 527, 71 (1997).
3) A simple method for preparation of aryl 2,2,2-trifluoroethyl ethers
F. Camps, J. Coll, A. Messeguer, M. A. Pericas, Synthesis, 1980, 727.
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