Reaction of 1,2-Di(1-adamantyl)-2-thioxoethanone with Diazomethanes; 1,3- versus 1,5-Dipolar Electrocyclization of a Sterically Crowded Thiocarbonyl S-Methylide

• Autorzy: Mlostoń G. , Urbaniak K. , Nomura T. , Nakayama J. , Heimgartner H.
• Języki publikacji: EN

Abstrakty

EN

The reaction of 1,2-di(1-adamantyl)-2-thioxoethanone (4c) with diazomethane and 2-diazopropane yielded 2-acylthiiranes 6a and 6b, respectively, and no 1,3-oxathioles of type 7 were formed. The reaction course is explained via [2+3]-cycloaddition, elimination of N2, and 1,3-dipolar electrocyclization of the in ter me di ate acyl-substituted thiocarbonyl ylides of type 1. The fail ure of the competitive 1,5-dipolar electrocyclization is a result of the sterically unfavor able conformation 1a.

Słowa kluczowe

EN

[2+3] cycloaddition; electrocyclization; thiocarbonyl ylides; 2-thioxoketones; thiiranes

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 11
• Strony: 1945--1951
• Opis fizyczny: Bibliogr. 12 poz., rys.

Twórcy

autor

Mlostoń G.

autor

Urbaniak K.

autor

Nomura T.

autor

Nakayama J.

autor

Heimgartner H.

• Department of Organic and Applied Chemistry, University of Łódź, Narutowicza 68, PL-90-136 Łódź, Poland,

Bibliografia

• 1.            a) Mlostoń G. and Heimgartner H., in '1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products', Eds. Padwa A. and Pearson W.H., J. Wiley & Sons, New York, 2002, p. 315; b) Mlostoń G. and Heimgartner H., Polish J. Chem., 74, 1503 (2000).
• 2.            Mlostoń G. and Heimgartner H., Targets in Heterocyclic Systems, 9, 141 (2005).
• 3.          Mlostoń G. and Heimgartner H., Targets in Heterocyclic Systems, 10, 266 (2006).
• 4.            Mlostoń G. and Heimgartner H., Curr. Org. Chem., in press.
• 5.            a) Bak C. and Praefcke K., Chem. Ber, 112, 2744 (1979); b) Bak C. and Praefcke K., J. Heterocycl. Chem., 17, 1655 (1980).
• 6.            Egli D.H., Linden A. and Heimgartner H., Helv. Chim. Acta, 89, 1910 (2006).
• 7.            a)Nakayama J.,Takahashi K., Watanabe T., Sugihara Y. and lshii A., Tetrahedron Lett., 41,8349(2000); b) Nakayama J., Takahashi K., Ono Y, Morita M., Sugihara Y. and Ishii A., Heteroatom Chem., 13,424 (2002).
• 8.            Petit M., Linden A., Mlostoń G. and Heimgartner H, Helv. Chim. Acta, 11, 1076 (1994).
• 9.            a)Kägi M., Linden A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 11,1299 (1994); b)Kägi M., Linden A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta, 79, 855 (1996).
• 10.          Kägi M., Linden A., Heimgartner H. and Mlostoń G., Helv. Chim. Acta, 76, 1715 (1993).
• 11.          Mlostoń G. and Heimgartner H, Helv. Chim. Acta, 15, 1825(1992).
• 12.          a) Capozzi G., Ottana R., Romeo G. and Maruzzi F., Gazz. Chim. ltd., 115, 311 (1985); b) Chan W., Courtneidge J.L., Davies A.G., Neville A.G., Evans J.C. and Rowlands Ch.C, J. Chem. Soc. Perkin Trans. 2, 2017(1986).