1961
DOI: 10.1002/jlac.19616490107
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Enamine, V. Alkylierung von Enaminen aus cyclischen Ketonen

Abstract: Athyl-propyl-butyl-acetaldehyd. -Aus Athyl-butyl-allyl-acetaldehyd in 91 -proz. Ausbeute. Nach Apfelsinenschalen riechende Flussigkeit vom Sdp.10 83 -85". -IR-Spektrum (als Film) : 1725 cm-I (C=O), keine C=C-Bande. 2.4-

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Cited by 32 publications
(4 citation statements)
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“…A mechanistic investigation of this cyclization indicates that an oxyallyl-Fe(ll) intermediate is involved.16 Less versatile use of 2-cycloheptenones has been made so far. 2-Cycloheptenone itself (5) has been brominated in a single step to 2,4,7-tribromotropone, which has then been catalytically reduced to tropone (Scheme I, step a').17 2-Cycloheptenone is available either via dehydrohalogenation of 2-chloroor 2-bromocycloheptanone (which are easily obtained from cycloheptanone),18 or by allylic bromination of cycloheptene followed by hydrolysis and oxidation19 (Scheme III). A further route to 5 is by thermal rearrangement of amethyltropidine (6) to 7 and acid hydrolysis of the latter.20…”
Section: Synthesismentioning
confidence: 99%
“…A mechanistic investigation of this cyclization indicates that an oxyallyl-Fe(ll) intermediate is involved.16 Less versatile use of 2-cycloheptenones has been made so far. 2-Cycloheptenone itself (5) has been brominated in a single step to 2,4,7-tribromotropone, which has then been catalytically reduced to tropone (Scheme I, step a').17 2-Cycloheptenone is available either via dehydrohalogenation of 2-chloroor 2-bromocycloheptanone (which are easily obtained from cycloheptanone),18 or by allylic bromination of cycloheptene followed by hydrolysis and oxidation19 (Scheme III). A further route to 5 is by thermal rearrangement of amethyltropidine (6) to 7 and acid hydrolysis of the latter.20…”
Section: Synthesismentioning
confidence: 99%
“…of this type may be found in the literature(Stork et al, 1954;Opitz and Mildenberger, 1961;Opitz et al, 1961). A mechanism such as this h i b i t e d .…”
mentioning
confidence: 76%
“…15 This compound contained 25 mol % of 1-methyl-2-pyrrolidinocyclohexene (1c), which could not be separated and was used as the mixture (1b/1c). Enamines-4-methyl-1-(1-pyrrolidinyl)cyclohexene (1f), 4-phenyl-1-(1-pyrrolidinyl)cyclohexene (1g), 1-(1-piperidinyl)cyclohexene (1h), and 1-(1-pyrrolidinyl)-2-methylpropene (1j)-were prepared in similar manner.…”
Section: Experimental Materialsmentioning
confidence: 99%