Studies on the Application of Lanthanoid Metalto Organic Reactions──The Reaction of Anhydrous NdCl3/Lithium Naphthalide System with Ketones or Isocyanates or Isothiocyanates

Chem. J. Chinese Universities ›› 1995, Vol. 16 ›› Issue (6): 881.

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Studies on the Application of Lanthanoid Metalto Organic Reactions──The Reaction of Anhydrous NdCl₃/Lithium Naphthalide System with Ketones or Isocyanates or Isothiocyanates

BAO Jian-Chun, BEI Mei-Zhi

Department of Chemistry Nanjing Normal University Nanjing 210024

Received:1994-06-18 Revised:1994-12-03 Online:1995-06-24 Published:1995-06-24

Abstract

Abstract: This paper reports the reactions of anhydrous NdCl₃/LiNp(LiNp=Lithium Naphthalide)system with benzoplienone,α,β-unsaturated carbonyl compounds,isocyanates and isothiocyanates, respectively.It is found that the anhydrous NdCl₃/LiNp system can promote a novel cyclodimerization of α,β-unsaturated carbony compound to give(IR^*,2S^*,3R^*,4S^*)-cyclopentanol derivatives and their stereoisomer.The same system can also react with isocyanates or isothiocyanates to give the corresponding reductive coupling products in good yield.We also found that the new system of NdCl₃/LiNp/Ligand,which differs from the NdCl₃/LiNp system, shows a different selectivity in the reaction with benzophenone to mainly give diphenyl methanol.

Key words: Active neodymium metal, Lithium naphthalide, Benzophenone α,β-Unsaturated carbonyl compound, Isocyanate

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BAO Jian-Chun, BEI Mei-Zhi. Studies on the Application of Lanthanoid Metalto Organic Reactions──The Reaction of Anhydrous NdCl₃/Lithium Naphthalide System with Ketones or Isocyanates or Isothiocyanates[J]. Chem. J. Chinese Universities, 1995, 16(6): 881.

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Studies on the Application of Lanthanoid Metalto Organic Reactions──The Reaction of Anhydrous NdCl₃/Lithium Naphthalide System with Ketones or Isocyanates or Isothiocyanates

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