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Journal Article

LICLO4 IN ETHER - AN UNUSUAL SOLVENT

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Waldmann, H. (1991). LICLO4 IN ETHER - AN UNUSUAL SOLVENT. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 30(10), 1306-1308. doi:10.1002/anie.199113061.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-9ADC-6
Abstract
Ionic reactions with polarized transition states are favored by the solvent system LiClO4/Et2O (3-5M). This is demonstrated by (hetero)Diels-Alder reactions and by the sigmatropic rearrangement of allyl vinyl ethers in this medium. The former react even faster and with higher endo selectivity than in water; the latter are not [3,3] but [1,3] sigmatropic rearrangements, which yield aldehydes. An important advantage of the LiClO4/Et2O system is it that may also be used for acceleration of reactions sensitive to hydrolysis.