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Reductive alkylation of aldehyde tosylhydrazones with organolithium reagents

✍ Scribed by E. Vedejs; W.T. Stolle

Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 194 KB
Volume: 18
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)92569-9

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✦ Synopsis

During unsuccessful attempts to generate dianions from aldehyde tosylhydrazones, we have

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dence for the rearrangement (2)+( 7). However, this isomerization can also be detected when (la) is used as starting material: Thus, on reaction of (la) with 6 equivalents of potassium tert-butoxide in THF at 35"C, the enol ether (10) is obtained in 44% yield. Its formation can be explained in terms