Chemilumineszierende Paracyclophane

Gundermann, Karl‐Dietrich; Röker, Klaus‐Dieter

doi:10.1002/ange.19730851011

Angewandte Chemie

1973

DOI: 10.1002/ange.19730851011

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Chemilumineszierende Paracyclophane

Karl‐Dietrich Gundermann

Klaus‐Dieter Röker

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1973

1979

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Cited by 14 publications

References 7 publications

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Sulfonpyrolyse als Synthesemethode

Vögtle¹,

Rossa²

1979

Angew. Chem.

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Cyclische Sulfone, die Strukturelemente wie aromatische Ringe, Heteroatome, funktionelle Gruppen und weitere SO,-Ciruppen als Ringglieder enthalten, zerfallen beim Erhitzen unter Abspaltung von SO, und Bildung einer neuen C -C-Bindung. Diese ,,Sulfonpyrolyse" ist in den letzten zehn Jahren zu einer allgemein anwendbaren Methode ausgeweitet worden, mit der sich auch sterisch gespannte mittel-und vielgliedrige Cyclen und Polycyclen synthetisieren lassen, die aromatische Ringe enthalten. Durch Pyrolyse halbseitig benzylischer Sulfone ist die Uberbruckung von aromatischen Systemen durch beliebig lange (CH,),-Ketten moglich. Au-Rerdem konnen (CH,),-Ketten zusammen mit zwei SO,-Molekiilen unter Rekombination der verbleibenden Zentren abgespalten werden, wodurch Ringverengungen um vier bis n Atome gelingen. Die Sulfonpyrolyse hat jedoch nicht nur Bedeutung als Ringverengungsmethode, sondern auch als wichtiger SchluRschritt bei der Synthese vielgliedriger Kohlenwasserstoffcyelen, z. B. vom Typ der Phane. I I Pyrolyse acyclischer und drei-bis siebengliedriger cyclischer SulfoneDie Sulfone ZZZ, R', R2 = Alkyl, Aryl, gehoren zu den am langsten bekannten organischen Verbind~ngen['~. Sie zeich-0044-8244u/79/0707-M34 $ 02 SO/O Angew C'hem. 91. 534-144 f197VI

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Sulfonpyrolyse als Synthesemethode

Vögtle¹,

Rossa²

1979

Angew. Chem.

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Pyrolysis of Sulfones as a Synthetic Method [New synthetic methods (28)]

Vögtle

Rossa

1979

Angew. Chem. Int. Ed. Engl.

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Cyclic sulfones containing structural elements such as aromatic rings, heteroatoms, functional groups, and further SO,-groups as ring members decompose on heating with cleavage of SO, and formation of a new C C bond. In the last decade this "sulfone pyrolysis" has been expanded into a generally applicable method even allowing the synthesis of sterically strained medium-membered and multi-membered cyclic and polycyclic systems containing aromatic rings. By the pyrolysis of sulfones which are only unilaterally activated by benzyl moieties, aromatic systems can be bridged by chains of any desired length. In addition, chains can be split off together with two SO2 molecules, with recombination of the remaining centers, resulting in ring contraction by four to n atoms. However, sulfone pyrolysis is of importance not only as a ring-contraction method but also as a crucial final step in the synthesis of multi-membered hydrocarbon cycles, e. g. of the phane type.

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Synthese vielgliedriger Kohlenwasserstoffringe durch mehrfache Ringkontraktion via Sulfonpyrolyse

Grütze

Vögtle

1977

Chem. Ber.

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A new method for the synthesis of many-membered hydrocarbon rings is described. Manymembered mono-or oligosulfides (e. g. 5) are oxidized to the corresponding sulfones (6). Pyrolysis of the latter yields the hydrocarbon rings (7). The new method not only allows the construction of ethano bridges but permits the synthesis of compounds containing bridges of different lengths between two aromatic systems. The bridge may contain hetero atoms, e. g. oxygen in 3-oxapentane units. A remarkable case is the extrusion of three SOz groups from the single bridge in compound 11 with formation of the hydrocarbon ring 7c in high yield. The new method was first used in the bridged o-terphenyl system, but it may also be applied to synthesize aliphatic bridges of different lengths between other aromatic rings, e. g. the biphenyl system or the m-terphenyl system. Under special conditions o-phenylene-bridged ring systems such as 13 may also be pyrolyzed successfully.

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Chemilumineszierende Paracyclophane

Cited by 14 publications

References 7 publications

Sulfonpyrolyse als Synthesemethode

Sulfonpyrolyse als Synthesemethode

Pyrolysis of Sulfones as a Synthetic Method [New synthetic methods (28)]

Synthese vielgliedriger Kohlenwasserstoffringe durch mehrfache Ringkontraktion via Sulfonpyrolyse

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