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Introducing Catalytic Lossen Rearrangements: Sustainable Access to Carbamates and Amines

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Abstract:

Abstract

A new, highly efficient and environmentally benign catalytic variant of the Lossen rearrangement is described. Dimethyl carbonate (DMC) as green activation reagent of hydroxamic acids in presence of catalytic amounts of tertiary amine bases {1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD), 1,8‐biazabicyclo 5.4.0 undec‐7‐ene (DBU), 1,4‐diazabicyclo[2.2.2]octane (DABCO), and triethylamine} and small quantities of methanol initiate the rearrangement. Methyl carbamates were obtained in good to moderate yields when aliphatic hydroxamic acids were employed in this catalytic Lossen rearrangement; under the same conditions aromatic hydroxamic acids yielded anilines. Notably, the mixture of DMC/methanol was recycled several times without observing decreased yields, thus minimizing the produced waste. Moreover, several other organic carbonates were successfully employed in the introduced catalytic Lossen rearrangement procedure.

Document Type: Communications

DOI: http://dx.doi.org/10.1002/adsc.201200760

Affiliations: Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany

Publication date: January 14, 2013

bpl/adsc/2013/00000355/00000001/art00012
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