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Addition of dithio esters and trithiocarbonates to 1-(diethylamino)propyne. Formation of α, β-unsaturated thioamides and vinylogous thioamides

✍ Scribed by V. H. M. Elferink; R. G. Visser; H. J. T. Bos

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
510 KB
Volume
100
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

α,β‐Unsaturated thioamides and vinylogous thioamides have been prepared by thermal addition of trithiocarbonates RS‐C(S)SR^1^ to 1‐(diethylamino)propyne. Aromatic dithio esters Ar‐C(S)SR only gave the α,β‐unsaturated thioamides. The dithio ester Me~2~CH‐C(S)SMe adds as acidic enethiol tautomer Me~2~CC(SH)SMe to 1‐(diethylamino)propyne. Reaction mechanisms and the stereochemistry of the adducts are discussed.

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ChemInform Abstract: Cooperative Activat
ChemInform Abstract: Cooperative Activation of Alkyne and Thioamide Functionalities; Direct Catalytic Asymmetric Conjugate Addition of Terminal Alkynes to α,β-Unsaturated Thioamides.
✍ Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki 📂 Article 📅 2011 🏛 John Wiley and Sons ⚖ 80 KB 👁 2 views

## Abstract Key feature of the title conjugate addition reaction is the cooperative activation of both the alkyne and the thioamide by a combined soft Lewis acid—hard Broensted base catalyst system.