アダマンタン関連橋頭位および橋かけ位アジドと三価リン化合物との反応

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タイトル別名
  • Reactions of Some Bridgehead- and Bridge-azides Related to Adamantane with Some Selected Trivalent Phosphorus Compounds
  • アダマンタン関連橋頭位および橋かけ位アジドと3価リン化合物との反応
  • アダマンタン カンレン キョウトウイ オヨビ ハシカケイ アジド ト 3カ リ
  • Synthesis of novel carbo- and heteropolycycles. VI. Reactions of some bridgehead- and bridge-azides related to adamantane with some selected trivalent phosphorus compounds.

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The reactions of 1-adamantyl azide [1 a], 2-adamantyl azide [1 b], , 2-methyl-2-adamantyl azide [1 c], , 3-homoadamantyl azide [1 d], , and bicyclo[3.3.1]non-1-y1 azide [1 e], with P(C6H5)3 [2 a], , P(n-Bu)3 [2 b], 1 and P(OEt)3 [2 c], were examined in order to prep are the corresponding iminophosphoranes. The relative reactivity of [1 a], in the reactions of [2a]-[2c], under reflux in benzene for 1 h was shown to be 1.0 0: 16.5: 8.50 based on the IR spectra. The relative reactivity of [2 a], in the reactions of [1 a]∼[1 e], under the same conditions as above was shown also as 1.00: 10.2: 0.58: 1.76. The corresponding iminophosphoranes [5 a], , [5 b], , and [5 c], from [1 a], with [2 b], and [2 c], , and from [1 b], with [2 a]respectively were obtained in high yields. Some examples of their applications on synthesis of adamantyl isocyanate, isothiocyanate, and carbodiimide, and/or their derivatives were also reported.

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