Synthessi of 3-Benzyl-1,3-thiazolidines by {2+3}-Cycloaddition of Sonochemically Generated Azomethine Ylides with Thiocarbonyl Compounds

Gebert, A.; Linden, A.; Mlostoń, G.; Heimgartner, H.

Artykuł - szczegóły

Tytuł artykułu

Synthessi of 3-Benzyl-1,3-thiazolidines by {2+3}-Cycloaddition of Sonochemically Generated Azomethine Ylides with Thiocarbonyl Compounds

Autorzy

Gebert A. , Linden A. , Mlostoń G. , Heimgartner H.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

Sonification of N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (5a) in the presence of LiF led to the formation of the reactive azomethine ylide 1d, which was intercepted by cyclic thioketones to give spirocyclic 1,3-thiazolidines. In the case of 2,2,4,4-tetramethylcyclobutane-1,3-dithione (13), the 1:1- and 1:2-cycloadduct, respectively, was formed as the major product depending on the ratio of the starting materials. With 1,3-thiazole-5(4H)-thiones, 1d undergoes stereoselective [2+3]-cycloadditions with the C=S group to yield spirocyclic 1:1-adducts. In the case of the 1,3-dipole generated from N-benzyl-N-(methoxymethyl)-N-[1-(trimethylsilyl)ethyl]amine (5b), the [2+3]-cycloaddition proceeded in a non-regioselective manner leading to a mixture of regio- and diastereoisomers.

Słowa kluczowe

azomethine ylides crystal structure 1,3-dipolar cycloadditions

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2003

Tom

Vol. 77 / nr 7

Strony

867--879

Opis fizyczny

Bibliogr. 52 poz., rys.

Twórcy

autor

Gebert A.

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

autor

Linden A.

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

autor

Mlostoń G.

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

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Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ1-0021-0047