492-17-1

Upstream product

• 84392-17-6 4'-(trifluoromethyl)-2-biphenylcarboxylic acid 
• 7664-93-9 sulfuric acid 
• 20972-43-4 trans-azoxybenzene 
• 7647-01-0 hydrogenchloride 
• 10035-10-6 hydrogen bromide 
• 108-88-3 toluene 
• 122-66-7 diphenyl hydrazine 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 1227476-15-4 Azobenzene 

Downstream Products

• 91822-41-2 4-(2-cyanophenyl)-aniline 
• 3477-62-1 2,4'-Diamino-4-nitro-biphenyl 
• 71857-67-5 4'-Acetamido-2-benzamido-4-nitro-biphenyl 
• 90-43-7 2-Phenylphenol 
• 4539-51-9 2-aminocarbazole 
• 113550-97-3 N,N'-disalicylidene-biphenyl-2,4'-diyldiamine 
• 92-67-1 4-phenylalanine 
• 42289-52-1 [1,1'-biphenyl]-2,4'-dicarbonitrile 
• 34883-43-7 2,4'-dichlorobiphenyl 

Relevant academic research and scientific papers

Anomals Schmidt reaction products of phenylacetic acid and derivatives

Treatment of carboxylic acids with sodium azide in sulfuric acid normally results in decarboxylation with conversion of the carboxylic acid to an amine (the Schmidt reaction). However, many side reactions have been reported to occur, particulary in the case of α-aryl carboxylic acids, such as sulfonation, direct amination of the phenyl ring, cyclization to a lactam, and elimination of side chains to give aniline. In this study, the reactions of a variety of analogues of phenylacetic acid under given reaction conditions are examined to determine which characteristics are important in the competing side reactions. Some reactions were carried out with TEMPO free radical as a radical scavenger to investigate whether direct amination proceeds by a radical intermediate. Phenylacetic acid is shown to give an ortho-aminated diamine product instead of the para-aminated one expected from direct amination. A mechanism for this side reaction, involving cyclization to a lactam intermediate followed by further cleavage, is proposed; an analogue of the hypothetical intermediate has been isolated for biphenylacetic acids.

Chronopotentiometric study of EC mechanism during the first cycle of alternating current

The theoretical approach to the application of the first period of a sinusoidal current at static and dynamic spherical electrodes for study of EC mechanism is presented. Methods for determining heterogeneous and homogeneous kinetic parameters are proposed. In order to check theoretical result, the rate of benzidine rearrangement was evaluated from transition time measurements.

The benzidine and diphenyline rearrangements revisited. 1-14C and 1,1′-13C2 kinetic isotope effects, transition state differences, and coupled motion in a 10-atom sigmatropic rearrangement

KIE were measured for 1-14C-and 1,1′-13C2-labeling in the acid-catalyzed rearrangement of hydrazobenzene (1) to benzidine (2) and diphenyline (3). Small KIE were found for forming 2, but none were found for the formation of 3. The results are consistent with concerted formation of 2 and nonconcerted formation of 3. KIE were remeasured for 4-14C-, 4,4′-13C2-, and 15N,15N′-labeling and were found to differ in magnitude from KIE reported earlier. The results are, nevertheless, consistent with the concerted formation of 2 and nonconcerted formation of 3. The differences in transition states for these two processes are discussed. Quantitative measurements of product distributions gave 85% 2 and 15% 3.

BOND-FORMING CARBON KINETIC ISOTOPE EFFECTS IN BENZIDINE REARRANGEMENTS

Kinetic isotope effects (KIE, k(12)C/k(13)C) have been measured for the acid-catalyzed rearrangement of N-2-naphthyl-N'-phenylhydrazine, 1, into 1-(o-aminophenyl)-2-naphthylamine, 2, and of hydrazobenzene, 3, into benzidine, 4, and diphenyline, 5.The KIE for formation of 2 was 1.0177, confirming the earlier diagnosis of concerted rearrangement.From the (13)C KIE, k(12)C/k(14)C is calculated to be 1.0339, as compared with the value 1.0287 obtained earlier with (14)C labelling and compensated for both intra- and intermolecular isotopic competition.The KIE for forming 4 and 5 were 0.9945 and 0.9953, respectively.The KIE for formation of 5 is thus experimentally the same as that for forming 4, for which , of course, the measured KIE in this case must be unity.Thus, the KIE obtained for 5 is consistent with forming 5 by a non-concerted pathway.The new result with labelling is consistent with earlier findings with 4- and 4,4'-carbon labelling.Collectively, the present results are used to illustrate potential problems with measuring and interpreting carbon KIE for bond-forming reactions.