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Synthesis 2001; 2001(3): 0427-0430
DOI: 10.1055/s-2001-11446
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Two New Methodologies for the Deoxygenation and Reduction of Nitrones Based on the Use of Lithium and DTBB (cat.) ‡

Gabriel Radivoy* , Gabriel Radivoy1 , Francisco Alonso, Miguel Yus
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain; Fax + 34(96)5 90 35 49; E-mail: yus@ua-es; URL: http://www.ua.es/dept.quimorg/
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Publication Date:
31 December 2001 (online)

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A variety of nitrones undergo deoxygenation when treated with an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB) (10 mol%) in THF at room temperature to give the corresponding imines. The Li/DTBB system, when combined with nickel(II) chloride dihydrate allows the reduction of a series of nitrones to secondary amines. The use of the deuterium oxide-containing nickel(II) salt transforms the starting nitrones to deuterated secondary amines.

nitrones - deoxygenation - reduction - nickel - Li/DTBB - imines - amines

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