ChemInform Abstract: Reactions of Ethyl Diazoacetate with Thioketones.

✍ Scribed by M. KAEGI; G. MLOSTON; H. HEIMGARTNER

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199829139

✦ Synopsis

Reactions of Ethyl Diazoacetate with Thioketones. -The 1,3-dipolar cycloaddition of ethyl diazoacetate (II) with thioketones is investigated. The most reactive dipolarophiles (I) give 1,3-dithiolanes, e.g. (III), (V), (VI) and (VIII). Sterically crowded thioketones (IX) and (XII) as well as the less reactive xanthione (XIV) give thiiranes which undergo spontaneous elimination of sulfur to give α,β-unsaturated esters such as (XI), (XIII) and (XV). -(KAEGI, M.;