This phenomenon allows for the stable isolation of stereoisomers that arise when the rotation of a single bond is restricted. Each stereoisomer is called an atropisomer. For example, in a biphenyl derivative (Figure (a)) that has a bulky substituent at the ortho position, the two benzene rings cannot form a coplanar structure, making it chiral, and since it cannot rotate around the bond connecting the two benzene rings, it can be optically resolved and two stereoisomers (a pair of enantiomers) can be stably isolated. In a triptycene derivative (Figure (b)), the rotation of the bond indicated by the thick line is restricted, and three stereoisomers can be stably isolated. Source: Morikita Publishing "Chemical Dictionary (2nd Edition)" Information about the Chemical Dictionary 2nd Edition |
単結合の回転が束縛されることによって生じる立体異性体が安定に単離できる現象.それぞれの立体異性体をアトロプ異性体という.たとえば,オルト位にかさ高い置換基をもつビフェニル誘導体(図(a))では,二つのベンゼン環が共平面構造をとれないためにキラルとなり,しかも二つのベンゼン環をつなぐ結合のまわりで回転することができないため,光学分割することができ,2種類の立体異性体(一対の鏡像異性体)が安定に単離される.またトリプチセン誘導体(図(b))では,太線で示した結合の回転が束縛されており,3種類の立体異性体が安定に単離されている. 出典 森北出版「化学辞典(第2版)」化学辞典 第2版について 情報 |
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