trans 2 -buten after hydroxlylation with performic acid gives
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Attempts to prepare dl-erythro-N,N-dimethyl-2,3-dihydroxy-3-phenylpropionamide by the usual organic peracid hydroxylation of dl-trans-N,N-dimethylcinnamamide gave unexpectedly a 40:60 mixture of both diastereomers, the threo form being predominant. The anomaly prompted a closer investigation of each of the intermediate stages in the overall hydroxylation process. Epoxidation of dl-trans-N,N-dimethylcinnamamide by monoperphthalic acid gave only dl-trans-N,N-dimethyl-3-phenylglycidamide. Opening of the epoxide ring by acids gave a mixture of dl-erythro and dl-threo diols in a ratio of 40:60. cis-N,N- Dimethyl-3-phenylglycidamide, when subjected to the same ring-opening processes, also gave a mixture, but in a ratio of 75:25.
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