Reaction of 2,2,4,4-Tetramethyl-3-thioxocyclobutanone with Dimethyl Diazomalonate Catalyzed by Rh2(OAc)4

• Autorzy: Mlostoń G. , Romański J. , Heimgartner H.
• Języki publikacji: EN

Abstrakty

EN

The reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1) with dimethyl diazomalonate in the presence of Rh2(OAc)4 in toluene at 50_C yielded a mixture of three products 10, 11, and 12. Thiocarbonyl ylide 8 is believed to be the common intermediate. The formation of 10 is rationalized by the 1,3-dipolar electrocyclization of 8 to give spirocyclic thiirane 9, which spontaneously eliminated sulfur. On the other hand, the 1,5- dipolar electrocyclization of 8 led to 1,3-oxathiole 11, which is converted into lactone 12 by hydrolysis.

Słowa kluczowe

EN

carbenoids; 1,3- and 1,5-dipolar electrocyclization; 1,3-oxathioles; thiiranes; thiocarbonyl ylides

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 4
• Strony: 551--555
• Opis fizyczny: Bibliogr. 17 poz., rys

Twórcy

autor

Mlostoń G.

• Section of Heteroorganic Compounds, University of Łódź, Narutowicza 68, PL-90-136 Łódź, Poland

autor

Romański J.

• Section of Heteroorganic Compounds, University of Łódź, Narutowicza 68, PL-90-136 Łódź, Poland

autor

Heimgartner H.

• Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Bibliografia

• 1. Mlostoń G., Romański J., Schmidt Ch., Reisenauer H.P. and Maier G., Chem. Ber., 127, 2527 (1994).
• 2. Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 79, 1785 (1996).
• 3. Mlostoń G., Romański J., Świątek A. and Heimgartner H., Helv. Chim. Acta, 82, 946 (1999).
• 4. Mlostoń G., Romański J. and Heimgartner H., Heterocycles, 50,403 (1999).
• 5. Review on thiocarbonyl ylides: Mlostoń G. and Heimgartner H., Polish J. Chem., 74, 1503 (2000).
• 6. Dawid M., Mlostoń G. and Warkentin J., Org. Lett., 3, 2455 (2001).
• 7. Mlostoń G., Romański J., Linden A. and Heimgartner H., Helv. Chim. Acta, 82, 1302 (1999).
• 8. Dawid M., Warkentin J. and Mlostoń G., Chem. Eur. J., submitted.
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• 11. Huisgen R., Mlostoń G. and Langhals E., Helv. Chim. Acta, 84, 1805 (2001).
• 12. Kagi M., Linden A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 81, 285 (1998).
• 13. Kelmendi B., Mlostoń G. and Heimgartner H., Heterocycles, 52,475 (2000).
• 14. Mlostoń G., Romański J., Linden A. and Heimgartner H., Polish J. Chem., 70, 595 (1996).
• 15. Mlostoń G., Romański J., Linden A. and Heimgartner H., Helv. Chim. Acta, 79, 1305 (1996).
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