Publication: Reaction of thiocarbonyl S-methylides with acetylenic dipolarophiles and an unexpected rearrangement of the cycloadducts
Reaction of thiocarbonyl S-methylides with acetylenic dipolarophiles and an unexpected rearrangement of the cycloadducts
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Gendek, T., Mlostoń, G., Linden, A., & Heimgartner, H. (2002). Reaction of thiocarbonyl S-methylides with acetylenic dipolarophiles and an unexpected rearrangement of the cycloadducts. Helvetica Chimica Acta, 85, 451–463. https://doi.org/10.1002/1522-2675(200202)85:2<451::AID-HLCA451>3.0.CO;2-9
Abstract
Abstract
Abstract
The 1,3-dipolar cycloaddition of 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-methylide (2a), generated in situ by thermal extrusion of N2 from the corresponding 2,5-dihydro-1,3,4-thiadiazole 1a, with electron-deficient acetylenic compounds yields spirocyclic 2,5-dihydrothiophene derivatives of type 4 (Scheme 2). Mixtures of diastereoisomers are obtained in the case of propiolates. The strained cyclooctyne also undergoes smooth cycloadditions with thioketone S-methylides (Scheme 3). Under acidic conditions, the spirocyclic products of
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- Gendek, Tomasz
- Mlostoń, Grzegorz
- Heimgartner, Heinz
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Citations
Gendek, T., Mlostoń, G., Linden, A., & Heimgartner, H. (2002). Reaction of thiocarbonyl S-methylides with acetylenic dipolarophiles and an unexpected rearrangement of the cycloadducts. Helvetica Chimica Acta, 85, 451–463. https://doi.org/10.1002/1522-2675(200202)85:2<451::AID-HLCA451>3.0.CO;2-9
