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An Unusual Reductive Ring-opening Reaction of Phthalimide with Sodium Hydride in DMF

An Unusual Reductive Ring-opening Reaction of Phthalimide with Sodium Hydride in DMF
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摘要 An unusual reductive ring-opening reaction of phthalimide with sodium hydride in anhydrous DMF was observed for the first time. The presumed mechanism was described in detail.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第7期777-778,共2页 中国化学快报(英文版)
关键词 PHTHALIMIDE BENZYLATION reduction ring-opening. Phthalimide, benzylation, reduction, ring-opening.
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参考文献3

  • 1[1]Lemieux R U,Takeda T,Chung,B Y,Am.Chem.Soc.Symposium Series,1976,39,90.
  • 2[2]Stangier P,Hindsgaul O,Synlett.,1996,179.
  • 3[3]Data for compound 6:[α]+30.6 (c 0.85,CHCl3).1H NMR (CDCl3,300 MHz):( 8.00 (m,1 H),7.48-7.12 (m,38 H),4.98~4.55 (m,7 H),4.46~4.36 (m,6 H),4.05~3.92 (m,3 H),3.87 (s,2 H,PhCH2),3.83-3.19 (m,24 H).13C NMR (CDCl3,75 MHz):( 171.2 (C=O),139.2,138.7,138.4,138.2,138.1,137.5,136.7,132.6,132.4,130.5,128.9,128.5,128.4,128.3,128.2,128.2,128.0,127.7,127.5,127.5,127.1,127.0 (aromatic carbon),103.9,102.5 (C-1,C-1'),82.7,81.7,80.1,76.5,75.1,74.8,74.7,73.6,73.5,73.2,73.0,70.6,70.5,70.3,69.0,68.8,68.7,68.4,53.5,52.2,48.3,47.5.MALDI-TOF MS (m/z):C78H87O15N,1238.3 [M+H]+.

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