Volume 27, Issue 18
Heterocyclic Compounds
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ChemInform Abstract: Hetero-1,3-Dipolar Cycloadditions of Dithiolane-Isocyanate Imminium Methylides: A Novel Route to 1,3-Oxazolidine- and Thiazolidine-2- thiones.

C. W. G. FISHWICK

C. W. G. FISHWICK

Sch. Chem., Univ. Leeds, Leeds LS2 9JT, UK

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R. J. FOSTER

R. J. FOSTER

Sch. Chem., Univ. Leeds, Leeds LS2 9JT, UK

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R. E. CARR

R. E. CARR

Sch. Chem., Univ. Leeds, Leeds LS2 9JT, UK

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First published: April 30, 1996

Abstract

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ChemInform Abstract

Treatment of the imminium salt (I) with CsF generates a dithiolane- isocyanate imminium methylide which is a new type of the azomethine methylide 1,3-dipole. It undergoes efficient and regioselective 1,3- dipolar cycloaddition with heterodienophiles (II) and (V) to form predominantly thiones (IV) and (VI) from the initial adducts via loss of thiirane.

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