Publication detail

Inverse neighboring group participation: New type of reaction mechanism

Authors: Hanusek Jiří | Váňa Jiří | Sedlák Miloš | Kammel Richard | Roithová Jana

Year: 2014

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Inverse neighboring group participation: New type of reaction mechanism	Recently, we have studied2 an unexpected course of rearrangement of S-(1(3H)-isobenzofuranone-3-yl)-N,N-dimethylisothiuronium bromide giving N,N’-dimethyl-N-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)-thiourea. A detailed experimental and DFT study of this S to N alkyl migration provided evidence for the existence of an unusual double displacement mechanism involving two consecutive back-side SN2 reactions where a carboxylate anion has a crucial role both as a leaving group as well as an internal nucleophile.	Inverse neighboring group participation; reaction mechanism

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