Summary
The action of proton acceptors on quaternary ammonium-or phosphonium-salts produces unusually reactive compounds, which are called N-ylids or P-ylens respectively. The N-ylids, which undergo the Stevens rearrangement, have found preparative application in newly developed syntheses of phenanthrene derivatives and cyclopolyenes. Appropriate representatives of the ylids are transformed into the formerly unknown isoindoles. The P-ylens also possess the noteworthy ability to convert aldehydes and ketones to the corresponding homogeneous olefines. With their help, new approaches to cyclopolyenes have been opened up, and naturally occurring substances containing polyene and polyenine chains, such asβ-carotene, oenanthetol and vitamin A, have been synthesized.
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References
W. Schlenk undJ. Holtz, Ber. dtsch. chem. Ges.50, 274 (1917).
G. Wittig und Mitarbeiter, Liebigs Ann. Chem.557, 193, 201 (1945).
G. Wittig undG. Felletschin, Liebigs Ann. Chem.555, 133 (1944).
G. Wittig undM. Rieber, Liebigs Ann. Chem.562, 177 (1949).
G. Wittig undM. Rieber, Liebigs Ann. Chem.562, 187 (1949).
H. Staudinger und Mitarbeiter, Helv. chim. Acta2, 638 (1919);4, 639, 897 (1921).
G. Wittig undG. Geissler, Liebigs Ann. Chem.580, 44 (1953).
G. Wittig undK. Torssell, Acta chem. Scand.7, 1293 (1953).
T. S. Stevens und Mitarbeiter, J. chem. Soc. London1930, 2107, 2119;1932, 69, 1932.
G. Wittig undH. Zimmermann, Chem. Ber.86, 629 (1953).
M. S. Newman undH. S. Whitehouse, J. Amer. chem. Soc.71, 3664 (1949).
G. Wittig und Mitarbeiter, Liebigs Ann. Chem.572, 3 (1951).
L. Fieser undM. M. Pechet, J. Amer. chem. Soc.68, 2577 (1946).
G. Wittig und Mitarbeiter, Liebigs Ann. Chem.593, 127 (1955).
Vgl. dazuK. Alder undH. Jacobs, Chem. Ber.86, 1529 (1953).
G. Wittig undW. Schoch, Liebigs Ann. Chem.572, 20 (1951).
G. Wittig und Mitarbeiter, Liebigs Ann. Chem.594, 89 (1955).
In den nicht frei existierenden Formen XVIIIa undb findet der Übergangszustand von XVII nach XIX seinen bildhaften Ausdruck.
G. Wittig und Mitarbeiter, Liebigs Ann. Chem.560, 116, (1948);572, 1 (1951).
G. Wittig undH. Laib, Liebigs Ann. Chem.580, 57 (1953).
G. Wittig undW. Haag, Chem. Ber.88, 1654 (1955).
G. Wittig undU. Schöllkopf, Chem. Ber.87, 1318 (1954).
G. Rapp, Diss. Tübingen 1955.
P. Duffner, Diplomarbeit Tübingen 1955.
U. Schöllkopf, Diss. Tübingen 1955.
Vgl.A. C. Cope undF. A. Hochstein, J. Amer. chem. Soc.72, 2515 (1950).
W. Stilz, Diss. Tübingen 1955.
Vgl.G. Wittig und Mitarbeiter, Liebigs Ann. Chem.563, 113 (1949).
H. H. Inhoffen und Mitarbeiter, Angew. Chem.67, 276 (1955).
F. Bohlmann undH.-G. Viehe, Chem. Ber.88, 1245, 1347 (1955).
Deutsche Bundes-Patent-Anmeldung der Badischen Anilin- und Sodafabrik, Ludwigshafen am Rhein (Erfinder:G. Wittig undH. Pommer).
G. Wittig, Angew. Chem.66, 10 (1954).
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Nach einem Vortrag, der in Zürich, in Basel und in Budapest Ende November 1955 gehalten wurde.
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Wittig, G. Synthesen über Stickstoff-ylide und Phosphor-ylene. Experientia 12, 41–48 (1956). https://doi.org/10.1007/BF02164669
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DOI: https://doi.org/10.1007/BF02164669