五員環状りん酸エステル類縁体の加水分解とその応用

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書誌事項

タイトル別名
  • Hydrolysis of Five-membered Cyclic Phosphate Analogs and Its Application to Organic Synthesis
  • ゴイン カンジョウ リンサン エステル ルイエンタイ ノ カスイ ブンカイ ト
公開日
1976
DOI
  • 10.5059/yukigoseikyokaishi.34.137
公開者
公益社団法人 有機合成化学協会

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説明

The mechanism of the hydrolysis of ethylenephosphates has been reviewed critically. It was pointed out that 1) the direct evidence for the formation of the pentacoordinate intermediate is necessary to establish the Westheimer's mechanism 2) the Westheimer's mechanism may not always applicable to the hydrolysis of five-membered cyclic phosphates. From this point of view, the hydrolysis of hetero atom substituted ethylenephosphates and vinylenephosphates have been reviewed and the following two extreme mechanisms were suggested to operate in the hydrolysis of five-membered cyclic phosphate analogs.<BR>1) Associative pentacoordinate intermediate mechanism with the exclusive formation of the ring retention product.<BR>2) Direct displacement mechanism with the exclusive formation of the ring cleavage product.<BR>Furthermore, a novel phosphorylation method of alcohols using the ring strain of vinylenephosphates analogs was introduced.

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