Intramolekulare Cycloadditionen Mit Azomethin‐Yliden: Synthese und NMR‐Untersuchungen einiger Paracyclophan‐Derivate vom Makrolid‐Typ

Eberbach, Wolfgang; Heinze, I.; Knoll, Katja; Fritz, Hans; Borle, François

doi:10.1002/hlca.19880710214

Cited by 11 publications

References 40 publications

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Intramolekulare Cycloadditionen mit Nitriloxiden: Untersuchungen zur Synthese von Heterophanen

et al. 1989

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Intramolecular Cycloadditions with Nitrile Oxides: Investigations towards the Synthesis of HeterophanesThe intramolecular cycloaddition reactions of the nitrile oxides 30a-d, 35, 36, and 47, obtained in situ from the 2,5-difunctional furan hydroximoyl chlorides 12a, b, 18 and the nitro compounds 9c,d, 21, 29, are described. With 3Oc the expected isoxazolofuranophane of type 31 is formed in acceptable yield; the additionally formed regioisomer 32c and the dimer 34c are very minor products in this case. Whereas the highest hornologue 30d gives a complex product mixture with small amounts of 31d and the macrocycle 34d as the only identified compounds, the derivatives bearing a shorter side chain (30a,b; n = 1, 2) give rise to the exclusive reaction of the dipole with a double bond of the furan system (to give 33a,b). The same behavior is obseped in the case of the electronically and sterically modified dipole systems 35/36 and 47, resp.; in spite of the much more favorable conditions for the formation of cyclophanes the cycloadditions result in the exclusive formation of the heterotricycles 41, 42 and 49. Possible preparative applications of the isomeric cycloaddition compounds are discussed.schen Ringe wurden in einer neuartigen Makrolid-Synthese die 16-gliedrigen Lactone 2/3 erhalten.Im allgemeinen erfolgt der Aufbau von Heterophanen entweder ausgehend von dem bereits gebildeten Ringsystem durch normale Heterocyclensynthese [Weg (a) in Schema 13 oder durch Cyclisierungsreaktion von entsprechend disubstituierten Heterocyclen (b). Wir haben bei der Synthese von 1 und analogen Derivaten das zweite Prinzip insofern variiert, als der Ringschlul3 uber eine intramolekulare 1,3-dipolare Cycloaddition erfolgt und damit gleichzeitig ein zweiter heterocyclischer Ring entsteht (c). In dieser Arbeit berichten wir uber die Einzelheiten solcher Cycloadditionen Schema 1

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Intramolekulare Cycloadditionen mit Nitriloxiden: Untersuchungen zur Synthese von Heterophanen

et al. 1989

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ChemInform Abstract: Intramolecular Cycloaddition Reactions with Azomethine Ylides: Synthesis and NMR Investigations of Some Macrolide‐Type Paracyclophanes.

et al. 1988

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255ChemInform Abstract The cis-(IV) and trans-(V) aziridines which are prepared starting from the readily available ester (I) undergo thermal intramolecular cycloadditions to give the diastereomeric paracyclophanes (VI)-(IX). As it can be seen from the low yields of (VIa)/(VIIa) and (VIIIa)/(IXa), a useful application of this method for preparing paracyclophane compounds is restricted to derivatives with more than 11 bridging atoms. The configuration of the five-membered heterocycles of the products and the conformational flexibility of the bridges is investigated.

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High dilution reactions — New synthetic applications

Knops

Sendhoff

Mekelburger

et al. 1992

Topics in Current Chemistry

105

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Intramolekulare Cycloadditionen Mit Azomethin‐Yliden: Synthese und NMR‐Untersuchungen einiger Paracyclophan‐Derivate vom Makrolid‐Typ

Cited by 11 publications

References 40 publications

Intramolekulare Cycloadditionen mit Nitriloxiden: Untersuchungen zur Synthese von Heterophanen

Intramolekulare Cycloadditionen mit Nitriloxiden: Untersuchungen zur Synthese von Heterophanen

ChemInform Abstract: Intramolecular Cycloaddition Reactions with Azomethine Ylides: Synthesis and NMR Investigations of Some Macrolide‐Type Paracyclophanes.

High dilution reactions — New synthetic applications

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