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Synthesis of new 2,3-perfluoroalkyl- and perfluoroaryl-1,4-diazabutadienes (α-diimines)

✍ Scribed by Bruce N. Diel; Peter J. Deardorff; Catherine M. Zelenski

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
282 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reaction of either decafluorobenzil or perfluorobiacetyl with two equivalents of Li[N(SiMe3)2], followed by quenching with C1SiMe3, provides N,N'-bis(trimethylsilyi)-1,2-bis(pentafluorophenyl)ethanediimine 1 and N,N'bis(trimethylsilyl)-1,1,1,4,4,4-hexafluoro-2,3-butanediimine 2, respectively. These represent the first examples of perfluoroalkyl-and perfluoroaryl-substituted diazabutadienes. Both compounds have been characterized based on 13C NMR, IR, elemental analysis and, for 1, single crystal X-ray crystallographic structure determination. Compound 1 crystallizes in the C21c space group, with a=20.3203(9) X, b=6.0758(3) X, c=-19.7948(9) X, or=90 °, 1~=106.2903(7) °, "~=90 °.

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[2+2]- AND [4+2] cycloaddition reactions
[2+2]- AND [4+2] cycloaddition reactions of 1,3-diazabutadienes with diphenylketene
✍ Peter Luthardt; Ernst-Ulrich Würthwein 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 244 KB

&ii&R&: 1,3-Diazabutadienes react with diphenylketene in [2+2] -and [4+2] cycloaddition reacg$ons, depending on the substitution pattern. Spectroscopic data (IR, H-and C-WWR) and results of quantummechanical model calculations (ab initio 3-2lG) are presented. and reactions of 1,3\_diazabutadienes 1