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Thioalkylation of Meldrum's Acid with Dialdehydes. Isopropylidene cis-2-Hydroxy-6-phenylthiocyclohexane-1,1-dicarboxylate Derivatives

✍ Scribed by Martin Eberle; Alex Ghorai; Richard G Lawton

Book ID: 104258254
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 641 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10174-5

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✦ Synopsis

AbWrsct: Reaction of Meldmm'sacid, thiophenolend gluteraldehydein aqueous acetonitrile with piperidine acetate a~ords a yield of isopropylidenecis-2-hydroxy-6-phenylthioeyclohexarre-l,l-diearboxylate. The reactionis very general. It csrrbe appliedto dialdehydesderivedin a manywaysusingmerrydifferentthiok. @ 1997Elsevier Science Ltd. Gluteraldehyde[1], Meldrum'sacid [2] and thiophenol[3] with O.lVO piperidiniumacetate or proline reactin aqueousacetonitrileat roomtemperatureto givea 70%yieldof a singleadduct,isopropylidene cis-2hydroxy-6-phenylthiocyclohexane-l,l-dicarboxylate' [5]. Other thiols, includingp-thiocrcsol, thiolacetic acid, mercaptoethanol, o-mercaptobenzoicacid, etc., may replace the thiophenol.2 Ofien the sPirocYclic -11 \ o 1 HS 2

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