bluuebunny/crossref_metadata_2025_split huggingface dataset:
Ein Beitrag zur Stereochemie der S′E‐Reaktion: Die Protonierung eines optisch aktiven 1, 1‐Disilyl‐2‐alkens
Authors: Wetter Hansjürg , Scherer Paul 
Published: December 2004

A Contribution to the Stereochemistry of the S′E‐Reaction: the Protonation of an Optically Active 1, 1‐Disilyl‐2‐alkeneAn optically active, 1, 1‐disilyl‐2‐alkene 2 was reacted with CF3COOH and HBF4·OMe2 and furnished with loss of one silyl group and migration of the double bond the corresponding vinylsilane 4. Determination of the absolute configuration and enantiomeric excess of 2 and 4 showed the S′E‐reaction to proceed in the case of CF3COOH with 48% (74% anti/26% syn) and in the case of HBF4·OMe2 with 44% (72% anti/28% syn) stereoselectivity. Deuteriodesilylation with CF3COOD resulted in the exclusive formation of at C (3)‐monodeuteriated vinylsilane 4.
Approaches to the Synthesis of Cytochalasans. Part 4. Improved Synthesis of the Tetrahydroisoindoline Subunits Related to the Cytochalasins and Aspochalasins
Authors: Schmidlin Tibur , Burckhardt Peter E. , Waespe‐Šarčevic̀ Nada , Tamm Christoph 
Published: December 2004

AbstractA general scheme for the synthesis of the tetrahydroisoindolinone moiety of naturally occurring cytochalasans and unnatural analogs was developed. The key‐step consists of the intermolecular [2+4]cycloaddition of 4‐methylsorbinol (7) to an alkylidene malonic ester derivative such as 6, 9 or 10, obtained from the corresponding amino acids. The products obtained, 4a, 17, and 18 were converted to the desired lactams 5, 21, and 22.Cycloaddition of the diene alcohol 7 to the optically active alkylidene malonic ester derivative 9b (s. Footnote 5) prepared from L‐leucine gave compound 17b with 98% enantiomeric excess. The optical activity was retained during the conversion of 17b to the lactam 21b. The latter is a subunit for the synthesis of the aspochalasins.
Production of (+)‐(S)‐Ethyl 3‐Hydroxybutyrate and (‐)‐(R)‐Ethyl 3‐Hydroxybutyrate by Microbial Reduction of Ethyl Acetoacetate
Authors: Wipf Beat , Kupfer Ernst , Bertazzi Roberto , Leuenberger Hans Georg Wilhelm 
Published: December 2004

AbstractThe production of (S)‐ethyl 3‐hydroxybutyrate (2) from ethyl acetoacetate (1) in higher yields and with higher optical purity than with the usual procedures was achieved by continuous addition of the substrate 1 and sucrose to an aerated suspension of bakers' yeast. The microbial reduction of 1 by the fungus Geotrichum candidum LINK yields ‐ for the first time ‐ the antipode 3.
Synthesis and Biological Activities of C (5)‐N‐Spin‐Labeled Uridines and Related Derivatives
Authors: Bobst Albert M. , Ozinskas Alvydas J. , De Clercq Erik 
Published: December 2004

AbstractDirect introduction of a N‐atom in one step at C (5) of 5‐hydroxyuridine (4a) or 5‐hydroxy‐2′‐deoxyuridine (4b) by certain primary amines led to the synthesis of two novel C(5)‐N‐spin‐labeled nucleoside analogs and to several C(5)‐N‐aryl adducts. Substitution by 4‐amino‐2,2,6,6‐tetramethylpiperidinooxyl (3) at C(5) of 4a or 4b led to the spin‐labeled nucleosides 5‐[(1‐oxyl‐2,2,6,6‐tetramethyl‐4‐piperidinyl)amino]uridine and ‐2′‐deoxyuridine (2a and 2b, respectively). The analogous C(5)‐substituted aniline adducts 5‐anilino uridine (5a) and 5‐anilino‐2′‐deoxyuridine (5b) and the p‐toluidine adducts 5‐(p‐toluidino)uridine (6a) and 5‐(p‐toluidino)‐2‐deoxyuridine (6b) were also prepared. In addition, results of the antiviral and antimetabolic activity of some of these analogs are reported.
Cycloaddition von Chlorsulfonyliscyanat an «Maleinisoimide»
Authors: Capraro Hans‐Georg , Rihs Grety , Martin Pierre 
Published: December 2004

Cycloaddition of Chlorosulfonylisocyanate to ‘Maleic Isoimides’Cycloaddition reactions of chlorosulfonylisocyanate to ‘maleic isoimides’ are described. The not expected multifunctional (2:1)‐adducts 2 were converted to the crystalline compounds 3, whose structures were resolved by X‐ray analysis.
Nucleosides and Nucleotides. Part 21. Synthesis of a Tridecanucleoside Dodecaphosphate Incorporating the Unnatural Base 2 (1 H)‐Pyridone
Authors: De Bernardini Silvio , Graf Georg , Leach Colin A. , Bühlmayer Peter , Waldmeier Felix , Tamm Christoph 
Published: December 2004

AbstractThe modified nucleoside Πd (1) was used in the synthesis of the oligonucleotide d (TpTpΠpCpGpTpCpApApApApTpC). Diester methodology being unsatisfactory, the triester synthesis was investigated with the unnatural nucleoside. An improved method of nucleoside phosphorylation was developed for the synthesis of the fully‐protected nucleotide 2e. This molecule could be cleanly and selectively deprotected, and allowed the efficient synthesis of the desired oligonucleotide.
13C‐NMR.‐Spektren von Dicyanhydrochinonen und Dicyan‐p‐benzochinonen
Authors: Neidlein Richard , Kramer Walter , Leidholdt Rolf 
Published: December 2004

13C‐NMR. Spectra of Dicyanohydroquinones and Dicyano‐p‐benzoquinonesThe 13C‐NMR. spectra of 12 dicyanohydroquinones and fully substituted dicyano‐ and diazido‐p‐benzoquinones have been measured and assigned by comparison with related benzene and p‐benzoquinone derivatives. For p‐benzoquinones the influence of the cyano and azido substituents on the chemical shift of the CO‐, α‐ and β‐C‐atoms has been investigated.
Fundamental Aspects of Ionic Dissociations: The Fragmentation Pathways of Excited Bicyclobutane Cations
Authors: Bombach Rolf , Dannacher Josef , Stadelmann J.‐P. , Neier Reinhard 
Published: December 2004

AbstractA most recently developed method to quantify the fragmentation pathways of excited radical cations is presented. Using bicyclobutane cation as an illustrative example, the RRKM analysis of the breakdown diagram determined by He‐Iα photoelectron‐photoion coincidence spectroscopy is outlined. The results imply complete isomerization to 1,3‐butadiene cation preceding the dissociative processes. The rate‐energy functions of four competitive primary fragmentation reactions, leading to C3H, C4H, C4H and C2H are established. There is compelling evidence that the production of C2H fragment ions does not compete effectively with these four reactions. The extent of kinetic and competitive shift effects is determined. The derived enthalpies of formation are in excellent accord with the available high quality reference data. The relative importance of different fragmentation pathways which ultimately lead to fragment ions of identical mass to charge ratio is assessed.
Synthesen Makrocyclischer Lactone durch Ringerweiterung. Vorläufige Mitteilung
Authors: Kostova Kalina , Hesse Manfred 
Published: December 2004

AbstractSyntheses of Macrocyclic Lactones by Ring Enlargement ReactionA general method is given for the synthesis of macrocyclic lactones by ring enlargement of 2‐nitrocycloalkanones by four ring members. By this procedure 2‐nitrocyclooctanone (1) is transformed to 8‐oxo‐dodecan‐11‐olid (5) in an overall yield of 63,5% and 2‐nitrocyclododecanone to 12‐oxo‐hexadecan‐15‐olid with 60% yield.
TETRAMETHOPRIM and PENTAMETHOPRIM: Synthesis, Antibacterial Properties and X‐Ray Structures
Authors: Brossi Arnold , Sharma Padam N. , Takahashi Kimio , Chiang Joseph F. , Karle Isabella L. , Seibert Gerhard 
Published: December 2004

AbstractTETRAMETHOPRIM (9) and PENTAMETHOPRIM (10), both prepared from the corresponding benzaldehydes 3 and 6 by conventional procedures, did not exhibit noteworthy antibacterial activity in vitro. A single crystal X‐ray analysis of 9 and 10 provided evidence that the out‐of‐plane methoxy groups in the two compounds created a completely different topographical situation to that present in TRIMETHOPRIM, and less ideal for the binding to bacterial dihydrofolate reductase.
Stereochemische Korrelationen zwischen (2R,4′R,8′R)‐α‐Tocopherol, (25S,26)‐Dihydroxycholecalciferol, (–)‐(1S,5R)‐Frontalin und (–)‐(R)‐Linalol
Authors: Barner Richard , Hübscher Josef 
Published: December 2004

Stereochemical Correlations between (2R,4′R,8′R)‐α‐Tocopherol, (25S,26)‐Dihydroxycholecalciferol, (–)‐(1S,5R)‐Frontalin and (–)‐(R)‐LinalolThe optically active C5‐ and C4‐building units 1 and 2 with their hydroxy group at a asymmetric C‐atom were transformed to (–)‐(1S,5R)‐Frontalin (7) and (–)‐(3R)‐Linalol (8) respectively; 1 and 2 had been used earlier in the preparation of the chroman part of (2R,4′R,8′R)‐α‐Tocopherol (6a, vitamin E), and for introduction of the side chain in (25S,26)‐Dihydroxycholecalciferol ((25S)‐4), a natural metabolite of Vitamin D3. The stereochemical correlations resulting from these converions fit into a coherent picture with those correlations already known from literature and they confirm our earlier stereochemical assignments. A stereochemical assignment concerning the C(25)‐epimers of 25,26‐Dihydroxycholecalciferol that was in contrast to our findings and that initiated the conversion of 1 and 2 to 7 resp. 8 for additional stereochemical correlations has been corrected in the meantime by the authors [26].
Studies Related to Biological Detoxification of Kraft Pulp Mill Effluent. VI. The Biodegradation of 12,14‐dichlorodehydroabietic acid with mortierella isabellina
Authors: Kutney James P. , Dimitriadis Eugene , Hewitt Gary M. , Salisbury Philip J. , Singh Mahatam , Servizi James A. , Martens Dennis W. , Gordon Robert W. 
Published: December 2004

AbstractA detailed study of the biodegradation of one of the fish toxic chlorinated resin acids, 12,14‐dichlorodehydroabietic acidThe correct IUPAC‐name is 12,14‐dichloro‐8,9,11,12‐tetradehydro‐7,8‐dihydroabietic acid.
(3) is presented. When exposed to the fungus Mortierella isabellina, 3 is converted into a number of hydroxylated and keto derivatives which show low levels of toxicity to fish. These metabolites were isolated and characterized.
New Synthetic Bromination Procedures for Use in Radiolabelling‐Chemistry: Reaction of C‐Metallated Derivatives of Carbohydrates with Bromide, in the Presence of Mild Oxidizing Agents
Authors: Neeser Jean‐Richard , Hall Laurance D. , Balatoni Julius A. 
Published: December 2004

AbstractIn the presence of 2 mol‐equiv. of AcONa, both triglycosylborane 1 and dicyclohexylglycosylborane 2 readily react with bromine chloride generated in situ from bromide and N‐chlorosuccinimide (NCS) to give the bromo‐sugar 3 (75 and 60%, resp.). The use of the BH3‐THF/bromide/NCS/2 AcONa procedure permits the rapid, face‐specific synthesis of 6 (58% uptake of bromine) and face‐selective synthesis of 8/9 (71% uptake of bromine), from vinyl ether derivatives 5 and 7, respectively. The dicyclohexylborane/bromide/NCS/2 AcONa procedure leads to the fast and quantitative conversion of 11 to the bromosugar 12 (91%). Hydroboration‐transmetallation sequences give access to C‐mercuriated carbohydrates 13 (71%) and 14 (78%). The bis(glycosyl)mercury derivative 13 is spontaneously cleaved by reaction with one equivalent of bromide/chloramine‐T/aqueous HCl‐solution to give 3 (87%) and 14 (76%). Hydrostannylation of acetylenic sugar 15 gave the (E)‐stannylvinyl derivative 16 as the major product. This latter precursor 16 is spontaneously cleaved by the bromide/chloramine‐T/aqueous HCl‐solution reagent to give the bromovinyl‐sugar 17 (96%).
Synthesis of D‐ and L‐5‐Oxaproline and of a New Captopril Analogue
Authors: Vasella Andrea , Voeffray Robert , Pless Janos , Huguenin René 
Published: December 2004

AbstractThe 1,3‐dipolar cycloaddition of the C‐t‐butyloxycarbonyl‐N‐mannosyl‐nitrone 5, formed in situ from the partially protected D‐mannose‐oxime 3 and the glyoxylate 4, to ethylene gave preferentially the (3S)‐N‐glycosyl‐isoxazolidine 6 which was transformed into the 3‐isoxazolidine‐carboxylate (L‐5‐oxaproline ester) 12 and into some derivatives thereof. The (S)‐configuration of 12 was proved by chemical correlation with a derivative of L‐asparagine. The D‐5‐oxaproline ester was obtained from the corresponding N‐ribosyl‐nitrone 24. Two protected dipeptides containing either C‐terminal‐ (28) or N‐terminal‐5‐oxaproline (= Opro) (30) were synthesized. Starting from 12, the analogue 1 of captopril® (2) was prepared and its activity as an inhibitor of the angiotensin‐converting‐enzyme (ACE) was examined.
Synthesis and Protonation Features of 24‐, 27‐ and 32‐membered Macrocyclic Polyamines
Authors: Dietrich Bernard , Hosseini Mir Wais , Lehn Jean‐Marie , Sessions Richard B. 
Published: December 2004

AbstractThree macrocyclic polyamines [24]ane‐N6 1, [32]ane‐N8 2 and [27]ane‐N6O3 3 of ring size 24, 32 and 27, respectively, have been synthesized. They contain either trimethylenediamine of ethylenediamine units. The acyclic analog 4, as the reference compound, was also prepared. Compounds 1–3 are macrocyclic analogs of natural polyamines and are potential ligands for metal cations as well as, when protonated, for anions. The protonation constants of compounds 1–4 have been determined. They are high enough for compounds 1–4 to be fully protonated in a pH‐range close to neutrality, as required for binding of anions of weak acids. The effect of structural features on the protonation constants are briefly discussed in relation to the design of macrocyclic polyamine ligands.
Face Selectivity of the Diels‐Alder Reaction of 5,6‐Bis((D)methylidene)‐2‐bicyclo[2.2.2]octene
Authors: Avenati Macro , Vogel Pierre 
Published: December 2004

AbstractThe face selectivity (endo‐face vs. exo‐face attack onto the exocyclic s‐cis‐butadiene moiety) of the [4+2]cycloadditions of 5,6‐bis((D)methylidene)‐2‐bicyclo‐[2.2.2]octene (11) to strong dienophiles has been determined in benzene at 25°. It is ca. 95/5, 75/5, 70/30, 60/40 and 50/50 for N‐phenyltriazolinedione (NPTAD), tetracyanoethylene (TCE), dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA) and singlet oxygen (1O2), respectively. The endo‐face preference is probably due to a participation of the homoconjugated double bond at C(2), C(3) which makes the etheno bridge more polarizable than the ethano bridge in 11. The absence of face selectivity with 1O2 is consistent with an entropy‐controlled mechanism involving the intermediacy of an exciplex.
Complexes macrocycliques des lanthanides: Stabilité et comportement électrochimique dans le méthanol et le carbonate de propylène
Authors: Almasio Marie‐Christine , Arnaud‐Neu Françoise , Schwing‐Weill Marie‐José 
Published: December 2004

Macrocyclic Complexes of Lanthanides: Stability and Electrochemical Behaviour in Methanol and Propylene CarbonateThe stabilities of the 1:1 complexes of the trivalent lanthanides with the diazapolyoxamacrocycles (2.1.) and (2.2.1.) in anhydrous methanol and propylene carbonate have been determined at 25°, by competitive potentiometric methods using H+ or Ag+ as auxiliary cations, with Et4NClO4 as supporting‐electrolyte. Additional data are also reported for the crown ethers 15C5 and 18C6 in propylene carbonate.It is shown that the diazapolyoxamacrocycles are much stronger complexing agents for trivalent lanthanides than macrocyclic polyethers, and that the bicyclic (2.2.1.) cryptates are more stable than the monocyclic (2.1.) complexes. With increasing atomic number of the lanthanides, the stability increases with diazapolyoxamacrocycles and decreases with cyclic polyethers.The electrochemical reduction of the trivalent samarium and europium cryptates has been investigated by polarography on a dropping Hg‐electrode, in water and methanol. In both solvating solvents, the +2 oxidation states of the cations are stabilized by complexation.
Versuche zur Synthese von ‘Push‐Pull’‐Diacetylenen
Authors: Stämpfli Urs , Neuenschwander Markus 
Published: December 2004

Attempted Synthesis of Push‐Pull DiacetylenesTwo alternative synthesis of push‐pull diacetylenes of type 1 (5‐amino‐2,4‐alkadiynals) are investigated. A bromination‐dehydrobromination sequence starting with 5‐dimethylamino‐2,4‐pentadienal (2) as well as the application of the well‐known Cadiot‐Chodkiewicz coupling reaction give new intermediates 3–5, and 7 and 8, respectively, but fail to give the target molecules 1.
The Vitamin‐B12‐derived Co(III)‐Complex ‘Pyrocobester’ as Photosensitizer and as Substrate in Reactions Involving ‘Singlet Oxygen’
Authors: Kräutler Bernhard , Stepánek René 
Published: December 2004

AbstractThe vitamin‐B12 derivative ‘pyrocobester’ (1) acts as photosensitizer in its light‐induced oxygenation which involves ‘singlet oxygen’ (1O2) and which gives ‘5,6‐dioxosecopyrocobester’ (2) cleanly. The identity of the photosensitizer is deduced from a match of the ‘photochemical action spectrum’ of the photooxygenation with the UV/VIS absorption spectrum of 1. The involvement of 1O2 in this reaction is established on the basis of solvent and solvent H/D isotope effects, of quenching studies with β‐carotene and of competition experiments with 9,10‐dimethylanthracene. Also, decomposition of the thermal 1O2‐source 1,4‐dimethylnaphthalene‐1,4‐endoperoxide in a solution of 1 induces a clean oxygenation of 1 to 2 in the dark as well.
Crystal and Molecular Structure of 2,3,5,6,7,8‐Hexamethylidenebicyclo [2.2.2]octane (‘[2.2.2]hericene’)
Authors: Pinkerton A. Alan , Schwarzenbach Dieter , Pilet Olivier , Vogel Pierre 
Published: December 2004

AbstractThe title molecule 1 has virtual D3h‐symmetry in the crystalline state.
Two‐Dimensional NMR Studies of Polyene Systems. I. All‐trans‐Retinal
Authors: Wernly Jacques , Lauterwein Jürgen 
Published: December 2004

AbstractTwo‐dimensional (2‐D) NMR results are presented for all‐trans‐retinal. 2‐D J‐resolved 1H‐NMR separated the multiplets of the olefinic protons and accurately determined their chemical shifts. 2‐D shift‐correlated 1H‐NMR gave the connectivities between scalar coupled protons. From the observed H,H long‐range couplings the assignment of the methyl resonances was possible. 2‐D J‐resolved 13C‐NMR separated overlapping C,H‐multiplets and allowed analysis of the C,H long‐range couplings, 2‐D shift‐correlated 13C‐NMR related each directly bonded C,H‐pair in this molecule. The potential of 2‐D NMR in resolving and identifying individual resonances in polyene spectra is discussed.
Attempts at Solvolytic Generation of Phenyl Cations
Authors: Laali Khosrow , Szele Ivanka , Yoshida Katsuhira 
Published: December 2004

AbstractNew substrates and reaction conditions which may be expected to yield phenyl cation intermediates have been investigated. The approaches used were: (a) solvolysis of PhX in fluorinated alcohols, where X = N (O) = NOTs (tosyloxyazoxy), N (O) = NONf (Nf = C4F9SO) and OSO2\documentclass{article}\pagestyle{empty}\begin{document}$ \mathop {\rm N}\limits^{\rm + } $\end{document} (CH3)3ŌTf (Tf=CF3SO); (b) solvolysis of ArBr, PhOTf and PhOSO2\documentclass{article}\pagestyle{empty}\begin{document}$ \mathop {\rm N}\limits^{\rm + } $\end{document}(CH3)3ŌTf (phenyl ‘betylate triflate’) in super‐acid solvents (FSO3H · SbF5, SbF5, AgSbF6). Analysis of the product mixtures provided no evidence for the intermediacy of phenyl cations as a major pathway in any of the reactions. This result is remarkable, since the ‘betylate’, for example, is a better leaving group by a factor of at least 105 than the ‘super’ leaving group triflate in the solvolysis of alkyl sulfonates. These results are a further indication of the extremely low stability of phenyl cations, as well as of the very special properties of the nitrogen leaving group in arenediazonium ions.
A Demonstrated Example of Competing D and Id Mechanisms for Dimethylformamide Exchange on the Octakis (dimethylformamide)‐erbium (III) Ion
Authors: Pisaniello Dino L. , Helm Lothar , Zbinden Donald , Merbach André E. 
Published: December 2004

AbstractDimethylformamide exchange on [Er(DMF)8]3+ is shown to take place via two competing dissociative‐type mechanisms: D and Id. It is concluded that a mechanistic crossover occurs along the series Tb‐Yb and this behaviour is contrasted with the changeover observed for the solvent exchange on the first‐row transition metal ions.
Zur Lenkung der intramolekularen Diels‐Alder‐Reaktion von Cyclopentadienen mit olefinischen Substituenten
Authors: Wallquist Olof , Rey Max , Dreiding André S. 
Published: December 2004

On the Course of the Intramolecular Diels‐Alder‐Reaction of Cyclopentadienes with Olefinic SubstituentsThe 1:3 mixture of 4‐bromobicyclo [3.2.0]hept‐2‐en‐6‐one and ‐7‐one (1/2), available by N‐bromosuccinimide bromination of bicyclo [3.2.0]hept‐2‐en‐6‐one, reacted rapidly with the organo‐magnesium and ‐zinc reagents 3, 10a, 10b and 10d by cyclobutanone ring opening and bromide ion expulsion to give the 5‐substituted cyclopentadienes 5, 12a, 12b/12c, and 12d as non‐isolated intermediates. Further transformation occured in situ either by a direct intramolecular Diels‐Alder reaction (path a) or by a [1,5]‐H‐migration prior to the intramolecular Diels‐Alder reaction (path b). The intermediate 5 followed only path a to give the bridged norbornene derivative 7, the intermediates 12a, 12b and 12c followed only path b to give the annellated norbornene derivatives 15a, 15b and 15c, respectively, and the intermediate 12d followed both paths to give the bridged 14d and the annellated norbornene derivative 15d (in the ration of about 1.4:1). These observations are discussed in terms of the relative velocities of [1,5]‐H‐migrations and intramolecular Diels‐Alder reactions. The major conclusions are: (1) bridged norbornene derivatives with a six‐membered ring C (such as 14d) can be prepared by an intramolecular Diels‐Alder reaction from 5‐alkenyl‐cyclopentadienes 12, as long as the dienophilic double bond is activated by an appropriate substituent (as in 12d); (2) such 5‐alkenyl‐cyclopentadienes 12 are available from the reaction of the bromo‐bicyclo‐heptenones 1/2 with suitable C‐nucleophiles 10.
Total Synthesis of Neplanocin A
Authors: Jung Michael , Offenbächer Gustav , Rétey János 
Published: December 2004

AbstractThe first total synthesis of racemic neplanocin A (1)After submitting our paper we learned that Arita et al. [J. Am. Chem. Soc.105, 4049(1983)] synthesized the natural enantioner of Neplanocin A.
from cyclopentadiene and acylnitroso‐3,5‐dinitrobenzoic acid is described. The synthesis is suitable for specific isotopic labelling of the hydroxymethyl group of neplanocin A.
Mechanism of Azo Coupling Reactions XXXIII. pH‐dependence and micromixing effects on the product distribution of couplings with 6‐amino‐4‐hydroxy‐2‐naphthalenesulfonic acid. Evidence for N‐coupling of a naphthylamine derivative
Authors: Kaminski Rafal , Lauk Urs , Skrabal Peter , Zollinger Heinrich 
Published: December 2004

AbstractAzo coupling of 6‐amino‐4‐hydroxy‐2‐naphthalenesulfonic acid (1) with 3‐trifluoromethyl‐ and 4‐nitrobenzenediazonium ion in relative highly concentrated aqueous alkaline solutions gave ratios of aminoazo to hydroxyazo compounds which are much higher than expected on the basis of the acid‐base pre‐equilibria of 1. These product ratios are disguised by effects of micromixing. In dilute solution (≤10−2 mol/l) product ratios and kinetics both correspond to the theory of acid‐base pre‐equilibria. A bisazo dye 10 was formed as a by‐product in couplings with 3‐trifluoromethylbenzediazonium ion, as expected for reactions with micromixing effects. In the reaction with benzenediazonium ions, the products of azo coupling of diazotized 1 with 1 (compound 8) and of the monoazo compound 8 with benzenediazonium ion (compound 9) were found. It is likely that diazotized 1 is formed by N‐coupling of 1 with benzenediazonium ion, tautomeric rearrangement and protonation of the triazene to diazotized 1 and aniline. This seems to be the first case of N‐coupling of a naphthylamine which was assumed to be capable of C‐coupling only.