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LiClO 4 in Ether—an Unusual Solvent
Author(s) -
Waldmann Herbert
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199113061
Subject(s) - solvent , sigmatropic reaction , chemistry , yield (engineering) , selectivity , ionic bonding , hydrolysis , ether , medicinal chemistry , organic chemistry , materials science , ion , catalysis , metallurgy
Ionic reactions with polarized transition states are favored by the solvent system LiClO 4 /Et 2 O (3–5 M ). This is demonstrated by (hetero) Diels–Alder reactions and by the sigmatropic rearrangement of ally1 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 LiClO 4 /Et 2 O system is it that may also be used for acceleration of reactions sensitive to hydrolysis.