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Further contributions to the stereospecificity of 1,3-dipolar cycloadditions of thiocarbonyl ylides

✍ Scribed by Rolf Huisgen; Eike Langhals; Heinrich Nöth

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
276 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereospecific cycloadditions of thiobenzophenone S-methylide (4) to dimethyl 2,3_dicyanofumarate and of thiocarbonyl ylide 1 to maleonitrile contribute to the separation of electronic (HO-LU energy distances) and steric effects in the borderline region of competing concerted and two-step processes.

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A thiocarbonyl ylide generated by sila-Pummerer rearrangement of bis(trimethylsilylmethyl) sulfoxide reacted with C6o to give a tetrahydrothiophene-fused C6o derivative. The cycloadduct was readily oxidized with mCPBA to give the corresponding sulfoxide and sulfone derivatives, which are useful for