Publication: Hetero-Diels-Alder-Reaktion mit 1,3-Thiazol-5(4H)-thionen
Hetero-Diels-Alder-Reaktion mit 1,3-Thiazol-5(4H)-thionen
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Tromm, P., & Heimgartner, H. (1988). Hetero-Diels-Alder-Reaktion mit 1,3-Thiazol-5(4H)-thionen. Helvetica Chimica Acta, 71(8), 2071–2084. https://doi.org/10.1002/hlca.19880710825
Abstract
Abstract
Abstract
On heating in toluene to 180° and on treatment with BF3.Et2O in CH2Cl2 at room temperature, 1,3-dienes react with the C=S group of 1,3-thiazol-5(4H)-thiones 1 in a reversible Diels-Alder reaction to give spiro[4.5]- heterocycles of type 6. A 1:1 mixture of two regioisomeric cycloadducts is formed in the thermal reaction with 2-methylbuta-1,3-diene (isoprene, 5b). In contrast, the formation of one regioisomer is strongly preferred in the BF3-catalyzed reaction. Frontier-orbital control as well as steric factors seem to be responsible f
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- Tromm, Peter
- Heimgartner, Heinz
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F. Hoffmann-La roche AG, Basel
Citations
Tromm, P., & Heimgartner, H. (1988). Hetero-Diels-Alder-Reaktion mit 1,3-Thiazol-5(4H)-thionen. Helvetica Chimica Acta, 71(8), 2071–2084. https://doi.org/10.1002/hlca.19880710825
