Purported Synthesis of 3,4,7,8-Tetraphenyl-1,2,5,6-tetraazocine from Benzil and Hydrazine: Competing Cyclization and Carbon–Carbon σ-Bond Scission

Author:

Eisch John J.,Chan Tsz Y.,Gitua John N.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Reference13 articles.

1. The synthesis and the antiaromatic character of dibenz[,,1]azapentalenes

2. Novel conjugated imines are of ongoing importance in our organometallic chemistry both as ligands for subvalent transition-metal complexes (cf. inter alia, J. J. Eisch, X. Ma, K. I. Han, J. N. Gitua, C. Krueger, Eur. J. Inorg. Chem. 2001, 77–88 ) and as substrates for epimetalation or reductive dimerization (cf., e.g., J. J. Eisch, J. R. Alila, Organometallics 2000, 19, 1211–1213).

3. Das 3,4,7,8-Tetraphenyl-1,2,5,6-tetraaza-cyclooctatetraen

4. Über 1.2.5.6-Tetraaza-cyclooctatetrane-(2.4.6.8)

5. Metze makes the following statements in ref.[3] without giving any experimentally determined values or analyses: (1) “Analyse und Molekulargewichtsbestimmung ergaben die Bruttofomular C28H20N4”; and (2) “Die Substanz..wird erst durch halbkonzentrierte Schwefelsäure bei 210–220 °C unter Druck hydrolytisch in Benzil und Hydrazin aufgespalten im Molverhältnis 1:1”. Both these statements would require actual experimental values and detail to be considered scientifically credible.

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