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Thioalkylation of Meldrum's Acid: Protected alkylidene derivatives of isopropylidene malonate

✍ Scribed by Martin Eberle; Richard G. Lawton

Book ID: 102856970
Publisher: John Wiley and Sons
Year: 1988
Tongue: German
Weight: 640 KB
Volume: 71
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19880710816

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✦ Synopsis

On reacting Meldrum's acid with butyraldehyde in MeCN in the presence of catalytical amounts of piperidine, we obtained a 52 % yield of the dimer ii (m.p. 1 17-1 18"), probably the same compound that was believed to be the Michaeladduct iii [13]. Reduction of dimer ii with NaBH, [5c] gave the corresponding alkane (m.p. 65-67"; dec.). Eg., with THF or CH2C12 as solvent and proline or hydrazine as catalyst. The same phenomenon has been observed in the case of adducts of cyclic tertiary amines [17].

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