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Solvent-free synthesis of nitrones in a ball-mill

Solvent-free synthesis of nitrones in a ball-mill
Solvent-free synthesis of nitrones in a ball-mill
Various C-aryl and C-alkyl-nitrones were synthesized within 0.5–2 h via condensation of an equimolar amount of aldehydes and N-substituted-hydroxylamines under solvent-free conditions in a ball-mill apparatus. Reactions can be performed without the need of excluding air and moisture and yields the expected products with no need for further purification. The study has been complemented by Differential Scanning Calorimetry (DSC) and solid-state 13C MAS nuclear magnetic resonance experiments. We have also studied the temperature profile during the reaction. A comparative study with the corresponding solvent-free microwave activated reaction showed the superiority of the ball-milling method; 31 examples are described, including the synthesis of the anti-aging agent C-phenyl-N-tert-butyl nitrone (PBN) and one of its analogues C-2-pyridyl-N-tert-butylnitrone (2-PyBN
waste prevention, solid-state reactions, mechanochemical activation, nitrones, solvent-free reactions
0040-4020
5569-5576
Colacino, Evelina
24fb6c9a-3e55-4c3a-be91-01e855ed5d45
Nun, Pierrick
597b217a-6b59-44e2-9aeb-1081b84a9cf6
Colacino, Francesco Maria
19bc6a1f-3066-441f-852d-a06c48fd744b
Martinez, Jean
bc857a45-129f-47fd-9243-35daa7186acc
AndLamaty, Frederic
31850acb-5df9-4b48-9d8d-9fe2d0fd97ea
Colacino, Evelina
24fb6c9a-3e55-4c3a-be91-01e855ed5d45
Nun, Pierrick
597b217a-6b59-44e2-9aeb-1081b84a9cf6
Colacino, Francesco Maria
19bc6a1f-3066-441f-852d-a06c48fd744b
Martinez, Jean
bc857a45-129f-47fd-9243-35daa7186acc
AndLamaty, Frederic
31850acb-5df9-4b48-9d8d-9fe2d0fd97ea

Colacino, Evelina, Nun, Pierrick, Colacino, Francesco Maria, Martinez, Jean and AndLamaty, Frederic (2008) Solvent-free synthesis of nitrones in a ball-mill. Tetrahedron, 64 (23), 5569-5576. (doi:10.1016/j.tet.2008.03.091).

Record type: Article

Abstract

Various C-aryl and C-alkyl-nitrones were synthesized within 0.5–2 h via condensation of an equimolar amount of aldehydes and N-substituted-hydroxylamines under solvent-free conditions in a ball-mill apparatus. Reactions can be performed without the need of excluding air and moisture and yields the expected products with no need for further purification. The study has been complemented by Differential Scanning Calorimetry (DSC) and solid-state 13C MAS nuclear magnetic resonance experiments. We have also studied the temperature profile during the reaction. A comparative study with the corresponding solvent-free microwave activated reaction showed the superiority of the ball-milling method; 31 examples are described, including the synthesis of the anti-aging agent C-phenyl-N-tert-butyl nitrone (PBN) and one of its analogues C-2-pyridyl-N-tert-butylnitrone (2-PyBN

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More information

Published date: June 2008
Keywords: waste prevention, solid-state reactions, mechanochemical activation, nitrones, solvent-free reactions

Identifiers

Local EPrints ID: 71477
URI: http://eprints.soton.ac.uk/id/eprint/71477
ISSN: 0040-4020
PURE UUID: dff18fe9-1f49-4380-8902-a507e8b87bf3

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Date deposited: 12 Feb 2010
Last modified: 13 Mar 2024 20:27

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Contributors

Author: Evelina Colacino
Author: Pierrick Nun
Author: Francesco Maria Colacino
Author: Jean Martinez
Author: Frederic AndLamaty

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