The Pinacol Rearrangement of Benzopinacol with DMSO-SbCI5 (1: 1) complex and DMSO-TiCI4 ( 1: 1) complext

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  • YAMAMOTO Jiro
    Department of Materials Science, Faculty of Engineering, Tottori University;
  • YOSHIOKA Masaki
    Department of Materials Science, Faculty of Engineering, Tottori University;
  • TAKAHARA Motohide
    Department of Materials Science, Faculty of Engineering, Tottori University;
  • TUBOI Takashi
    Department of Materials Science, Faculty of Engineering, Tottori University;
  • ITOH Satoshi
    Department of Materials Science, Faculty of Engineering, Tottori University;

Bibliographic Information

Other Title
  • DMSO-SbC15(1:1)錯体およびDMSO-TiC14(1:1)錯体を用いたベンゾピナコールのPinacol転位
  • Study of synthesis using metallic complex. X. The pinacol rearrangement of benzopinacol with DMSO-SbCl5 (1:1) complex and DMSO-TiCl4 (1:1) complex.

Description

When a solution of benzopinacol (1) and DMSO-SbC15 (1: 1) complex (Complex A) (1: 1ratio) in nitromethane was allowed to stand at room temperature for 24 h, benzopinacolone ( 2 ) was obtained in quantitative yield. In this reaction, tetraphenylethylene oxide (3) was detected as an intermediate. The reaction seems to proceed according to the following stoichiometry.<BR>2 Ph2C-CPh2 DMSO-SbCI5→2 Ph3C-CPh + SbOCI3+ DMSO + H2O +2HC1<BR>The pinacol rearrangement of [1] over with O.15mol eequivalent of DMSO-TICI4(1: 1)complex (Complex B) proceeded quantitatively. In this case, both theoxygen atom and the chlorine atom sseem to participate in the formation of [2]as an oxidizing agent. Study of Synthesis Using Metallic Complex. X.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1990 (4), 430-433, 1990-04-10

    The Chemical Society of Japan

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