1127-42-0

Upstream product

• 558-17-8 tert-Butyl iodide 
• 98-95-3 nitrobenzene 
• 1102959-05-6 nitrobenzene radical anion sodium salt 
• 594-70-7 2-Methyl-2-nitropropane 
• 1623-99-0 phenyl sodium 

Downstream Products

• 38370-36-4 N-(tert-butyl)-[1,1'-biphenyl]-4-amine 
• 76577-40-7 2-(N-tert-butylamino)biphenyl 
• 76472-76-9 Trifluoro-methanesulfonic acid 4-tert-butylamino-phenyl ester 
• 57964-44-0 tert-Butyl-(2'-methyl-biphenyl-4-yl)-amine 
• 1131-29-9 N-t-butyl-p-benzoquinone imine N-oxide 
• 134810-69-8 C₁₅H₂₃NO₂ 
• 19617-94-8 2,5-bis(t-butylamino)-p-benzoquinone 
• 1520-99-6 2,5-bis(butylamino)-1,4-benzoquinone 
• 25295-92-5 2,5-bis(1,1,3,3-tetramethylbutylamino)-p-benzoquinone 
• 83933-71-5 2-(2,2,4,4-tetramethylpyrrolidin-1-yl)-p-benzoquinone 
• 106-51-4 p-benzoquinone 
• 7466-42-4 4-phenylazobenzene 

Relevant academic research and scientific papers

Reductive activation of arenes: XIV.Effect of medium on the products ratio in the alkylation of nitrobenzene radical anion sodium salt

The product of nitrobenzene reduction by 1 equiv of sodium reacted with tert-butyl iodide in liquid ammonia and its mixtures with tetrahydrofuran and hexamethylphosphoramide to afford a mixture of compounds alkylated either by the functional group (N-alkylation) or at the benzene ring (C-alkylation). The ratio of N-and C-alkylation products decreases in the solvents series NH3-THF (5.7) > NH3 (1.0) > NH3-HMPA (0.6).

Reductive Activation of Arenes. X. Effect of the Cation and Crown-Ether Additions on the Direction of tert-Butylation of Products of One-Electron Reduction of Nitrobenzene by Alkali Metals in Liquid Ammonia

Reaction of tert-butyl iodide with products of one-electron reduction of nitrobenzene by alkali metals (Li, Na, K, Rb, Cs) in liquid ammonia results in formation of compounds alkylated at the nitro group (N-alkylation) and the benzene ring (C-alkylation).The ratio of the N- and C-alkylated products (N/C) increases with increasing size of the alkali metal cation.Additions of crown ethers or sodium bromide and iodide, as well as variation of the concentration of the reduction product have almost no effect on the N/C value.Increased overall yield of the alkylation products and reduced N/C ratio were observed when the product of nitrobenzene reduction with potassium reacted with tert-butyl iodide in the presence of dicyclohexano-18-crown-6.

REDUCTIVE ACTIVATION OF ARENES. VI. REACTION OF THE PRODUCT OF THE ONE-ELECTRON REDUCTION OF NITROBENZENE BY SODIUM IN LIQUID AMMONIA WITH ISOMERIC BUTYL IODIDES

The reaction of the product of the reduction of nitrobenzene by one equivalent of sodium in liquid ammonia with n-butyl, sec-butyl, and isobutyl iodides leads to the corresponding N,O-dialkylphenylhydroxylamines as the major products through an SN2 mechanism.The analogous reaction with tert-butyl iodide gives approximately equal amounts of products of butylation in the benzene ring, namely, 4-tert-butylnitrobenzene and 4-tert-butylaniline, and at the nitro-group, namely, N-tert-butylaniline and N-tert-butylphenylhydroxylamine.The formation of these N-tert-butyl produ cts is probably the result of the transfer of an electron from the nitrobenzene radical-anion to the alkyl iodide and subsequent recombination of the tert-butyl radical with the nitrobenzene radical-anion.The increase in the fraction of tert-butylation at the nitro group in going from hexamethylphosphorotriamide or its mixture with tetrahydrofuran as the solvent to liquid nitrogen is probably a consequence of a greater role for interaction with the medium, which affects the distribution of the spin density in the nitrobenzene radical-anion or on the relative stability of the transition states responsible for the competing recombination pathways.