Interception of an Intermediate Thiocarbonyl Ylide by NH-Compounds

• Autorzy: Mlostoń G. , Janicka E. , Woźnicka M. , Linden A. , Heimgartner H.
• Języki publikacji: EN

Abstrakty

EN

By thermal decomposition of 1,1,3,3-tetramethyl-5-thia-7,8-diazaspiro[3.4]octan- 2-one (1), 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-methylide (2) was generated as an intermediate. This reactive "thiocarbonyl ylide" was trapped by protic agents such as alcohols, NH- and SH-acidic compounds to give 1,3-adducts of the acetal type. In a mixture of methanol and ammonia, the spiroheterocycle 1 was deprotonated and competitive ring opening of the 2,5-dihydro-1,3,4-thiadiazole and the cyclobutane ring occurred to give the hydrazono derivative 7 and the 1,3,4-thiadiazole 8, respectively. Surprisingly, 2 was intercepted by maleimide in a 1,3-dipolar cycloaddition.

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 12
• Strony: 1805--1817
• Opis fizyczny: Bibliogr. 38 poz., rys.

Twórcy

autor

Mlostoń G.

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

autor

Janicka E.

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

autor

Woźnicka M.

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

autor

Linden A.

• Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

autor

Heimgartner H.

• Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

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