Thionourethane

General structure of thionourethanes. Where:
R ¹ and R ² = aliphatic or aromatic radical or H
R ³ = aliphatic or aromatic radical, H, metal (in the case of salts )

As Thionourethane (also Thionurethane ) are referred to the representatives of a chemical substance group. These are the thione of unstable Thioncarbaminsäure (H ₂ N-CSOH). They are regioisomeric to the thiolourethanes .

The substance groups of thiono- and thiolourethanes are often summarized with the vague designation thiourethanes (synonym: thiocarbamates ).

Manufacturing

Thionurethanes can be prepared by esterifying isothiocyanates with alcohols :

meaning

Structural formula of tolciclate

Only a few thionourethanes are of technical importance. For example, tolnaftate and tolciclate are used as antimycotics .

Reactions

Thionourethanes aryl-substituted on the oxygen can be converted into the isomeric thiolourethanes by the Newman-Kwart rearrangement (also known as thiono-thiolo rearrangement ) .

Individual evidence

1. ^ Siegfried Hauptmann : Organic Chemistry , VEB Deutscher Verlag für Grundstoffindindustrie, Leipzig, 1985, p. 325. ISBN 3-342-00280-8 .
2. ↑ H. Kwart, ER Evans: The Vapor Phase Rearrangement of Thioncarbonates and Thioncarbamates. in: J. Org. Chem. , 1966, 31 (2), 410-413. doi : 10.1021 / jo01340a015