Studies on the Synthesis of Novel 4-Membered Cyclic Oxaphosphetanes via Intramolecular Mitsunobu Reaction of Bishydroxyalkylphosphinic acids

Studies on the Synthesis of Novel 4-Membered Cyclic Oxaphosphetanes via Intramolecular Mitsunobu Reaction of Bishydroxyalkylphosphinic acids
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双羟烷基次膦酸分子内光延反应合成新型四元环氧杂磷酸烷的研究

DOI:
10.1055/s-0035-1560426
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发表时间:
2016
期刊:
影响因子:
2
通讯作者:
and T. Yokomatsu
and T. Yokomatsu
中科院分区:
化学4区
文献类型:
--
作者:
B. Kaboudin;H. Haghighat;and T. Yokomatsu

文献摘要

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报道了以双羟基膦酸为原料合成新型四元环氧杂环己烷的研究。研究表明,在室温下,双羟基膦与三苯基膦和二异丙基偶氮二甲酸二异丙酯(DIAD)的混合物在甲苯-CH2Cl2中通过分子内Mitsunobu环化反应进行。用三苯基膦和DIAD的混合物处理双羟甲基膦酸的两个非对映异构体(dl对和Meso),只得到环氧杂环己烷的一个立体异构体。
Studies on the synthesis of novel four-membered cyclic oxaphosphetanes from bishydroxyphosphinic acids is reported. Investigations showed that the conversion proceeds through an intramolecular Mitsunobu cyclisation of bishydroxyphosphinic acids with a mixture of triphenylphosphine and diisopropylazodicarboxylate (DIAD) in toluene–CH2Cl2at room temperature. The treatment of two diastereomers of bishydroxymethylphosphinic acids (dlpair andmeso) with a mixture of triphenylphosphine and DIAD gives only one stereoisomer of the cyclic oxaphosphetane.