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The Metallation‐Elimination Reaction, II. Monocyclic Anions and Polyanions
Author(s) -
Wilhelm Dieter,
Clark Timothy,
Friedl Thomas,
von Ragué Schleyer Paul
Publication year - 1983
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19831160232
Subject(s) - chemistry , trimethylsilyl chloride , medicinal chemistry , methyl iodide , potassium , polymer chemistry , sodium hydride , butyllithium , trimethylsilyl , organic chemistry , catalysis
Equimolar mixtures of n ‐butyllithium and potassium tert ‐amyloxide effect metallation and metal hydride elimination of cyclic olefins directly to give conjugated anions and polyanions in a single operation. 1‐Methyl‐1‐cycloalkenes or methylenecycloalkanes are particularly well suited and give highly unsaturated products. Odd‐membered rings eliminate better than their even‐membered counterparts, and eight‐membered rings eliminate particularly slowly. Reactions with methyl iodide and trimethylsilyl chloride proceed smoothly in high yield.