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- W2097987906 abstract "Die elektronenreichen Olefine 1a–e sowie 7 bilden mit Schwefelkohlenstoff im Verhältnis 1:2 die stabilen Dipole 5a–e und 8; im Fall von 5f dient das Imidazolidin 6 als Edukt. Die Dipole werden durch Protonierung mit Acetylendicarbonsäure charakterisiert (Bildung der Imidazolidiniumsalze 9a–d). Mit den elektronenarmen Acetylenen 10a–g gehen die N-arylierten Dithioate 5d–f [3 + 2]-Cycloaddition ein, wobei die unsymmetrisch substituierten elektronenreichen Olefine 11a–k gebildet werden. Diese lassen sich, wie für 11a, e und g gezeigt wurde, mit einem weiteren Mol Acetylen 10a in die 1,3-Butadiene 15a–c umwandeln, wobei die [2 + 2]-Cycloaddukte 14a–c als Zwischenstufen der Reaktion angesehen werden. Die N-alkylierten Dipole 5a–c bilden mit den Acetylenen 10a–c, h und i im Molverhältnis 1:2 unmittelbar die 1,3-Butadiene 16a–i. Electron-rich Olefins, 6. — CS2 Dipoles from Electron-rich Olefins — Synthesis and Cycloaddition Reactions The electron-rich olefines 1a–e and 7 react with carbon disulfide in a molar ration of 1:2 to yield the stable dipoles 5a–e and 8; in the case of 5f the imidazolidine 6 is the starting material. The dipoles are characterized by protonation with acetylenedicarboxylic acid (formation of the imid-azolidinium salts 9a–d). The N-aryl-substituted dithioates 5d–f undergo [3 + 2] cycloaddition with electron-poor acetylenes to yield the unsymmetrically substituted electron-rich olefins 11a–k. These may be transformed, as was shown for 11a, e, and g, with a further mole of acetylene 10a into the 1,3-butadienes 15a–c, in which reaction the [2 + 2] cycloadducts 14a–c are regarded to be the intermediates. The N-alkyl-substituted dipoles 5a–c react with the acetylenes 10a–c, h, and i in a molar ration of 1:2 to furnish directly the 1,3-butadienes 16a–i." @default.
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- W2097987906 date "1982-08-19" @default.
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- W2097987906 title "Elektronenreiche Olefine, 6. CS2-Dipole aus elektronenreichen Olefinen — Herstellung und Cycloadditionsreaktionen" @default.
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- W2097987906 doi "https://doi.org/10.1002/jlac.198219820805" @default.
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