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Zwitterions as Intermediates of the 1,3-Dipolar Cycloaddition of Electrophilic Azides to 5-Alkylidenedihydrotetrazoles – the Other Non-Concerted Limiting Case

✍ Scribed by Prof. Dr. Helmut Quast; Dipl.-Chem. Dieter Regnat; Eva-Maria Peters; Dr. Karl Peters; Prof. Dr. Hans Georg von Schnering


Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
453 KB
Volume
29
Category
Article
ISSN
0044-8249

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✦ Synopsis


For the solid state investigations, the oligomer to be investigated was deposited onto a Pt-disk electrode (@ = 1 mm) by sublimation or by dipcoating the respective oligomer in dichloromethane. In this way, fully chargeable (iv ) homogenous layers of differing thickness could be prepared.

The amount of material employed was determined from the integral under the redox waves ( = charge). In the reduction of p-sexiphenyl the charge numbers of the redox steps could be derived unambiguously from the observed charge ratio of 2.1 for the first two redox steps (Table 1 b,c). In the case of quaterphenyl an experiment was carried out with a large electrode and a weighable amount of material; this gave a value of 2 for the charge number. A similar experiment with sexiphenyl confirmed the above described direct method for the quantitative measurement.

By reduction and oxidation of one and the same sample ofp-sexiphenyl it was confirmed that the integral under the first reduction wave is identical with that under the first oxidation wave (Ei = 1.65 V), i.e., two electrons per molecule are transferred in both cases.


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