1105707-49-0Relevant articles and documents
Synthesis of α-amino acids by umpolung of weinreb amide enolates
Hirner, Sebastian,Kirchner, Donata K.,Somfai, Peter
supporting information; experimental part, p. 5583 - 5589 (2009/05/11)
An efficient and diastereoselective synthesis of α-amino acids from readily available starting materials has been developed. The key feature of this reaction is an umpolung of a glycine-derived enolate, providing an alternative approach for the synthesis of α-amino acids. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
RADICAL-ANIONS OF AROMATIC COMPOUNDS. VII. REACTION OF THE PRODUCTS FROM THE REDUCTION OF NITROBENZENE BY SODIUM WITH ISOPROPYL AND tert-BUTYL IODIDES
Danilova, N. K.,Shteingarts, V. D.
, p. 701 - 708 (2007/10/02)
The reaction of the products from the reduction of nitrobenzene by one and two equivalents of sodium with isopropyl iodides leads to the formation of N,O-diisopropylphenylhydroxylamine, while the reaction with tert-butyl iodide leads to p-(tert-butyl)nitrobenzene.Such a change in the nature of the reaction product in the transition from the primary and secondary alkyl halides to the tertiary alkyl halides clearly results from a change in the SN2 mechanism to the SRN1 mechanism, involving transfer of an electron from the radical-anion or dianion of nitrobenzene to the alkyl halide.The formation of considerable amounts of azoxybenzene in the reaction with tert-butyl iodide shows that the dianion and, to a lesser degree, the radical-anion of nitrobenzene exhibit basic characteristics.
