Carbodiimide insertion into sulfonimides: one-step route to azepine derivatives via a two-atom saccharin ring expansionElectronic supplementary information (ESI) available: Experimental details, 1H and 13C NMR, MS and FTIR-ATR data. CCDC 1494031-1494039. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6cc07331j

A previously unknown insertion of carbodiimides into sulfonimides enables the first one-step, two-atom expansion of the saccharin 5-membered ring into a 7-membered benzo[1,2,4]thiadiazepine, and a two-atom chain extension of a non-cyclic sulfonimide. This reaction is enhanced by copper salts, which...

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Main Authors: Tan, Davin, Friš i, Tomislav
Format: Article
Language:English
Online Access:Get full text
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Summary:A previously unknown insertion of carbodiimides into sulfonimides enables the first one-step, two-atom expansion of the saccharin 5-membered ring into a 7-membered benzo[1,2,4]thiadiazepine, and a two-atom chain extension of a non-cyclic sulfonimide. This reaction is enhanced by copper salts, which allow it to be conducted mechanochemically, in a solvent-free manner. A novel carbodiimide insertion reaction enables a one-step, two-atom expansion of cyclic and linear sulfonimides, including the first direct expansion of saccharin into thiadiazepines.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc07331j