ChemInform Abstract: Reaction of Dirhodan and Thiocyanogen Chloride with Arylvinyl Ethers.

Abstract

The aryl‐vinyl ethers (I) add dirhodan (IIa) or thiocyanogen Chloride (IIb) to give the 1,2‐dithiocyanatoethylaryl ethers (IIIa) or the 1‐chloro‐2‐thiocyanatoethylaryl ethers (IIIb), the latter being produced regioselectively.

Amino-Thiocyanation of Electron Rich Olefins as an Efficient Purine and Pyrimidine N-Alkylation Process

“…We chose chlorothiocyanate (ClSCN) as a reactive electrophile based on its known chemistry of addition across carbon-carbon double bonds to give b-chlorothiocyanates. 6 We envisioned (Scheme 1) reaction of ClSCN with a fural to give a cyclic sulfonium ion that could be trapped with silylated heterocycle to give thiocyanate substituted nucleoside mimics. The trapping of this ion would be expected to give rise to trans addition stereochemistry in the final product.…”