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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 15-16
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Original Articles

Cycloaddition of Chlorosulfonyl Isocyanate to 2H-Azirines: Formation of [2+2+2] Cycloadducts

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Pages 1649-1655 | Received 29 Apr 1991, Published online: 23 Sep 2006
 

Abstract

Chlorosulfonyl isocyanata (CSI) reacts with 2H-azirines 1 a-c at -78°C to form [2+2+2] cycloadducts 3a-c and 4a-c. The tricyclic aziridine derivatives 4a-c undergo CSI extrusion reactions and subsequent oxidation to the corresponding pyrazines 5a-c. Structural identifications of 3a-c and 4a-c are based on ir, nmr and mass spectral data.

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