KETENE .23. CONFORMATIONAL CONTROL OF THE ADDITION-REACTIONS OF KETENES WITH N-PHENYLNITRONES
KETENE .23. CONFORMATIONAL CONTROL OF THE ADDITION-REACTIONS OF KETENES WITH N-PHENYLNITRONES
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DOI：
10.1039/p19850001837
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发表时间：
1985-01-01
期刊：
影响因子：
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通讯作者：
TAYLOR, GA
中科院分区：
文献类型：
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作者：
FALSHAW, CP;HASHI, NA;TAYLOR, GA
x射线分析表明（5a）中的硝基没有扭曲，反驳了先前与酮类反应形成恶唑烷酮而不是吲哚酮的解释。硝酮（5c）与二甲基烯酮和二苯基烯酮反应生成恶唑烷酮（6c,d），而硝酮（5d）和（5e）在类似条件下生成吲哚酮衍生物(9)。酮与硝基酮（5a-c）反应生成恶唑烷酮的原因是n -苯基键的旋转受限，阻止了吲哚酮生成前的[3,3]-迁移(3)→(4)。
X-Ray analysis shows that the nitrone group in (5a) is not distorted, disproving a previous explanation for the formation of oxazolidinones rather than indolones in the reactions with ketenes. Nitrone (5c) reacts with dimethylketene and diphenylketene to form oxazolidinones (6c,d) whereas nitrones (5d) and (5e) under similar conditions form indolone derivatives (9). Oxazolidinone formation by the reaction of ketenes with nitrones (5a–c) results from restricted rotation about the N-phenyl bond preventing the [3,3]-migration (3)→(4), which precedes indolone formation.