Addition of Diazomethane to Phosphonodithioformates and Reactions of Phosphonylated Thiocarbonyl S-Methylides

• Autorzy: Urbaniak K. , Mlostoń G. , Gulea M. , Masson S. , Heimgartner H.
• Języki publikacji: EN

Abstrakty

EN

The reaction of phosphonodithioformates 14 with diazomethane at -60 graduate C yielded 2,5-dihydro-1,3,4-thiadiazoles 15 as unstable intermediates. Their structure was evidenced by the base-catalyzed elimination of methylsulfane leading to 1,3,4-thiadiazole- 2-phosphonates. At ca. -35 graduate C, thermal decomposition of 15 by N2-elimination led to reactive thiocarbonyl S-methylides 17. In the absence of trapping reagents, these 1,3-dipoles undergo a head-to-head dimerization leading to 1,4-dithianes 18. An intermediate zwitterionic dimer 19 was detected by 31P NMR spectroscopy. The initially formed thiocarbonyl S-methylide 17 as well as an open-chain zwitterionic dimer 20 was intercepted by methanol. Stable interception products were also obtained with S- and N-nucleophiles.

Słowa kluczowe

EN

addition reactions; dimerization; thiocarbonyl ylides; 1,3-dipoles; sulfur heterocycles

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 9
• Strony: 1483--1494
• Opis fizyczny: Bibliogr. 31 poz., rys.

Twórcy

autor

Urbaniak K.

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

autor

Mlostoń G.

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

autor

Gulea M.

• Laboratory of Molecular and Thio-organic Chemistry, UMR-CNRS 6507, ENSI-Université de Caen,6, Bd. Du Maréchal Juin, F-14050 Caen, France

autor

Masson S.

• Laboratory of Molecular and Thio-organic Chemistry, UMR-CNRS 6507, ENSI-Université de Caen,6, Bd. Du Maréchal Juin, F-14050 Caen, France

autor

Heimgartner H.

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

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