1989
DOI: 10.1002/prac.19893310418
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Studies on the oxidation of enamines with molecular oxygen 2. Oxidation of 1‐Amino But‐1‐enes

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Cited by 13 publications
(4 citation statements)
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“…Evidently 15 arises via C-oxidation of spirocyclo-enediamine 3 (Scheme 8). Similar oxidation of enamines, enhanced in presence of molecular sieves was described previously by Blau et al [17][18][19] Eur (15) shown with 50 % probability thermal ellipsoids. The germanium-nitrogen bond in 3b (E = Ge) is less stable than a silicon-nitrogen bond and rapidly decomposes in the presence of air to give the cyclo-trigermoletrioxane 16 (Scheme 8), identified by X-ray crystallography and 1 H, and 13 C NMR analysis.…”
Section: Introductionsupporting
confidence: 72%
“…Evidently 15 arises via C-oxidation of spirocyclo-enediamine 3 (Scheme 8). Similar oxidation of enamines, enhanced in presence of molecular sieves was described previously by Blau et al [17][18][19] Eur (15) shown with 50 % probability thermal ellipsoids. The germanium-nitrogen bond in 3b (E = Ge) is less stable than a silicon-nitrogen bond and rapidly decomposes in the presence of air to give the cyclo-trigermoletrioxane 16 (Scheme 8), identified by X-ray crystallography and 1 H, and 13 C NMR analysis.…”
Section: Introductionsupporting
confidence: 72%
“…The best results were obtained with anisic acid and benzoic acid which gave the desired product in 78% yield (Table , entries 6 and 7). In contrast, the addition of strong acids (Table , entries 8 and 9) resulted in a too rapid release of the enamine which was decomposed before it could be converted efficiently by the catalyst. The yield was further improved by lowering the catalyst loading (Table , entry 10), and under optimized conditions (Table , entry 11), 3aa was detected in 93% yield.…”
mentioning
confidence: 99%
“…In the publications [l] and [2] we have described the results of the oxidation of aliphatic enamines with molecular oxygen. We showed that only products of an oxidative attack at the C = C double bond are formed and no products of an allylic oxidation, which are the main products in the oxidation of aliphatic and cycloaliphatic olefines.…”
mentioning
confidence: 99%