Bis(perfluoroalkyl)sulphur difluorides and bis(perfluoralkyl) sulphoxides

Sauer, Dennis T.; Shreeve, Jean’ne M.

doi:10.1039/c29700001679

Cited by 11 publications

(6 citation statements)

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“…[22] In this case, the electron-donating morpholino group accelerated the inverse electron demand DielsϪAlder reaction. [23] In this study, we chose to investigate, in particular, the DielsϪAlder reaction of alkynes with 3,6-di(2-pyridyl)-1,2,4,5-tetrazine, since this results directly in the desired 3,6di(2-pyridyl)pyridazines as depicted in Scheme 1. Moreover, for the preparation of a wide range of different 3,6-di(2pyridyl)pyridazines, it is not necessary to use alkenes in the synthetic route, since many alkynes are commercially available nowadays.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Novel Substituted 3,6‐Di(2‐pyridyl)pyridazine Metal‐Coordinating Ligands

2003

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The synthesis of novel functionalized 3,6-di(2-pyridyl)pyridazines via an inverse electron demand Diels−Alder reaction between the corresponding 3,6-di(2-pyridyl)-1,2,4,5-tetrazine and various alkynes is reported. The resulting 3,6-di(2-pyridyl)pyridazines were investigated using X-ray crystallography, IR spectroscopy, and NMR spectroscopy, whereby several 2D NMR spectroscopic techniques were exploited to

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Novel Substituted 3,6‐Di(2‐pyridyl)pyridazine Metal‐Coordinating Ligands

2003

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“….Auch in der Pyridazinreihe sind die 1,4-Dihydrodcrivate stabiler als die 1,ZDihydroverbindungen. So werden bei Diels-AZder-Reaktioncn von Tetrazinen mit Olefinen nicht die erwarteten 1.2sondcrn d i e 1,4-Dihydropyridazine isoliert [7] Abschliessend sei noch bemerkt, dass stereoisomere Formen sowohl bei den Hexahydro-s-tetrazinen als auch bei den 1,2,3,6-Tetrahydrotetrazinen nicht beobachtet wurden.…”

Section: )unclassified

“…DimethyZ-7,2,3,6-tetrahydro-s-tetrazin (3 1,3,4,6-TetramethyZ-7,4-dihydro-s-tetrazin (11 42 (9,7), 125 (8,O). 141 (7,8), 55 (7,6), 27…”

Section: Chromatogramm Mindestens 4 Komponenten)mentioning

confidence: 99%

Dihydro‐ und Tetrahydroderivate des 3,6‐Dimethyl‐1,2,4,5‐tetrazins

Skorianetz¹,

Kováts²

1972

Helvetica Chimica Acta

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The scheme 1 shows those tetrahydro‐ and dihydroderivatives of the 3,6‐dimethyl‐1,2,4,5‐tetrazine (or s‐tetrazine), 8, which are theoretically possible without considering cis‐trans isomerism, together with the reaction pathways. We did not succeed in synthetizing the 3,6‐dihydroderivative, 7, and could not isolate the 1,2‐dihydrocompound, 4, the latter being probably easily convertible to the thermodynamically more stable 1,4‐dihydro‐s‐tetrazine, 5, via their common conjugate base 4,5B. The 1,4‐dihydro‐s‐tetrazine, 5, gives with 3,6‐dimethyl‐s‐tetrazine 8, a charge transfer complex, 15. The same compounds form in acidic or basic aquious solution stable radicals, 16B and 16S. The mode of formation of these radicals and the subsequent reactions are depicted in scheme 2.

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“…Die CH,-Protonen treten bei 6 = 4.04 ppm als s auf. Die restlichen Protonen erscheinen bei 6 = 6,80 ppm (H-C(6/7)) und bei 6 = 7,42 ppm (H-C(5/8)) als m. Die Lage des AA',BB'-Systems bei 6 = 7,11 ppm (Zentrum) Verbindung 3 reagiert mit verschiedenen Nucleophilen schon bei Raumtemperatur unter Anlagerung an die (C=N)-Bindung [9]. So reagiert 3 mit EtOH, i-PrOH und Hydraziden wie tert -Butyl-hydrazinoformat, Methyl-hydrazinoformat und (2,CDinitro-pheny1)hydrazin zu den bisher in der Literatur unbekannten uberbriickten Phthalazin-Derivaten des Strukturtyps 4.…”

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“…IR (CH2C12): 3040,2960,2900, 1730, 1440, 1395, 1330, 1220, 1150, 1120,1070, 1020: 0,66 (d, J = 6,8,); 0,79 (d, J = 63, Ha-C(9)); 4,04 (s, 2 CH,O); 6,80 (m, H-C(6), H-C(7)); 7,42 (m, H-C (5), H-C (8)). I3C-NMR (62,89 MHz, CDC13): 26,18 (t, C(9)); 53,44(q, CH,O); 79,05 (s, C(4a), C(8a)); 125,48 (d, C(5), C(8)); 126,94 (dd, C(6), C(7)); 154,39 (s, C(I), C (4) (7), 63 (17), 62 (7), 59 (49, 51 (17), 49 (27), 44 (12). Anal.…”

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confidence: 99%