1971
DOI: 10.1002/ange.19710832006
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Pyridino‐protophane mit Alkylensegmenten wechselnder Länge

Abstract: rnit verlaufen die Cycloadditionen anscheinend stereospezifisch, was ebenso wie das Nichtauftreten von sieben-

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Cited by 18 publications
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“…The mechanistic significance of this observation has been questioned (Huisgen, 1984), however, because the isolated yields of the cycloadducts were rather low. The exclusive formation (Scheme 1) of a single 3-vinylpyrrolidine, (3), in the reaction of this anion with 1,3-dienes, (2) (Kauffmann & Eidenschink, 1971), would be additional evidence for a concerted cycloaddition, but quite recently, [4+3]-cycloaddition and 1,4-addition products [(5) and (6), respectively] were found to be formed in moderate yields when the 1,3-diphenyl-2-azaallyl anion, (1), was combined with 3,3,4,4,5,5-hexamethyl-1,2-bis(methylene)cyclopentane, (4) (Mayr et al, 1993) (Scheme 2). Both reaction partners showed ~4 reactivity resulting in the formation of a seven-membered ring.…”
mentioning
confidence: 99%
“…The mechanistic significance of this observation has been questioned (Huisgen, 1984), however, because the isolated yields of the cycloadducts were rather low. The exclusive formation (Scheme 1) of a single 3-vinylpyrrolidine, (3), in the reaction of this anion with 1,3-dienes, (2) (Kauffmann & Eidenschink, 1971), would be additional evidence for a concerted cycloaddition, but quite recently, [4+3]-cycloaddition and 1,4-addition products [(5) and (6), respectively] were found to be formed in moderate yields when the 1,3-diphenyl-2-azaallyl anion, (1), was combined with 3,3,4,4,5,5-hexamethyl-1,2-bis(methylene)cyclopentane, (4) (Mayr et al, 1993) (Scheme 2). Both reaction partners showed ~4 reactivity resulting in the formation of a seven-membered ring.…”
mentioning
confidence: 99%