1976
DOI: 10.1002/prac.19763180203
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Synthese von Heterocyclen durch CC‐Knüpfung. I. Edelmetall‐katalysierte Cyclisierung von Acrylsäure‐diallylamid

Abstract: Einwirkung von Palladiumchlorid auf Acrylsäure‐diallylamid 1 führt zu einem Gemisch von fünfgliedrigen Heterocyclen, wobei überwiegend Ringschluß zwischen der Acryloylgruppe und einer Allylgruppe erfolgt (Bildung von 2, 3, 4, 5 und 6), daneben Ringschluß zwischen den beiden Allylgruppen zu 7 und 8. Der letztere Fall überwiegt bei Rhodiumkatalyse (Bildung von 7); daneben entstehen geringe Mengen 4, 2 sowie ein weiteres Isomeres 14. Bei Anwendung größerer Rhodiummengen lassen sich N‐ständige Allylgruppen von Säu… Show more

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Cited by 29 publications
(9 citation statements)
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“…The palladium chloride mediated cycloisomerization of 1,6-dienes 26,27,29 proceeds under the same conditions as the reaction utilizing rhodium trichloride, however, in the case of palladium a different regiochemical outcome is observed. Obtention of the internal olefin is most likely due to in situ isomerization of the initially derived alkylidenecyclopentane (Equations 17 and 18).…”
Section: B Palladium Based Catalyst Systemsmentioning
confidence: 80%
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“…The palladium chloride mediated cycloisomerization of 1,6-dienes 26,27,29 proceeds under the same conditions as the reaction utilizing rhodium trichloride, however, in the case of palladium a different regiochemical outcome is observed. Obtention of the internal olefin is most likely due to in situ isomerization of the initially derived alkylidenecyclopentane (Equations 17 and 18).…”
Section: B Palladium Based Catalyst Systemsmentioning
confidence: 80%
“…For the case of rhodium, both rhodium trichloride 26 and Wilkinson's catalyst 27,28 have proven to be effective catalysts. Thus, 1,6-dienes 42 and 44 cycloisomerize in good yield to provide methylene cyclopentanes (Equations 15 and 16).…”
Section: Alkenes As Enophiles a Rhodium Based Catalyst Systemsmentioning
confidence: 99%
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“…A few years later the same cycloisomerisation catalysed by cationic Ni-phosphine complexes was studied extensively by Bogdanovic, 9 and Schmitz reported on the Pd-catalysed and the Rh-catalysed cycloisomerisation of N,N-diallyl acrylamide which gave a host of products (the Rh-catalysed process being marginally more selective). 10 Interestingly, the acrylamide moiety participated extensively in the Pd-catalysed process (giving lactams) whereas the opposite outcome was apparent with Rh (giving pyrollidine isomers). When the complexity of substrate (and thus product range) was reduced from a triene to a 1,6diene, in the form of N,N-diallyl amides (e.g.…”
Section: Origins and Evolution Of The Reaction Class 21 16-dienesmentioning
confidence: 99%
“…For example, both rhodium trichloride [22,23] and Wilkinson's catalyst [24,25] promote this reaction efficiently to give methylenecyclopentane 26 (Scheme 7.12). In the latter case, the active catalyst species is believed to be [Rh Rhodium(I) complexes have also been shown to promote metallo-ene type reactions efficiently (Scheme 7.14) [26].…”
Section: Cycloisomerization Of Dienesmentioning
confidence: 99%