Acyl C→N migration in the thioureidomethylation of 2-(4-methylbenzoyl)cyclohexanone

The thioureidomethylation of the sodium enolate of 2-(4-methylbenzoyl)cyclohexanone 3 with N-(tosylmethyl)thiourea 1a or N-(azidomethyl)thiourea 2 in acetonitrile results in the unexpected formation of N-(4-methylbenzoyl)- N’-[(2-oxocyclohexyl)-methyl]thiourea 6, which was structurally characterised...

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Bibliographic Details
Published in:Mendeleev communications 2004-01, Vol.14 (1), p.31-33
Main Authors: Shutalev, Anatoly D., Zhukhlistova, Nadezhda E., Gurskaya, Galina V.
Format: Article
Language:English
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Summary:The thioureidomethylation of the sodium enolate of 2-(4-methylbenzoyl)cyclohexanone 3 with N-(tosylmethyl)thiourea 1a or N-(azidomethyl)thiourea 2 in acetonitrile results in the unexpected formation of N-(4-methylbenzoyl)- N’-[(2-oxocyclohexyl)-methyl]thiourea 6, which was structurally characterised by X-ray diffraction analysis.
ISSN:0959-9436
1364-557X
DOI:10.1070/MC2004v014n01ABEH001866