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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 14
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Original Articles

Magnesium-Tin(II) Chloride Dihydrate: A New System for Chemoselective Reduction of Aldehydes into Alcohols in the Presence of Ketones, Ketalization of Ketones and Dehalogenation of Benzyl Halides

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Pages 2501-2506 | Received 02 Nov 1998, Published online: 17 Sep 2007

References

  • Larock , R. C. 1989 . Comprehensive Organic Transformations, A guide to Organic Functional Group Preparations , 175 – 198 . New York : VCH Publications Inc. .
  • Ward , D. E. and Rhee , C. K. 1989 . Can. J. Chem. , 67 : 1206 and references cited therein
  • Bordoloi , M. 1993 . Tetrahedron Lett. , 34 : 1681
  • Bordoloi , M. 1993 . J. Chem. Soc. Chem. Comm. , : 922
  • Lee , J. D. 1979 . A Concise Inorganic Chemistry , 175 – 198 . London : ELBS and Van Nostrand and Reinhold Co. Ltd. .
  • Spectral data of 2: 1H NMR (300MHz, Bruker Avance DPX 300, assignment by COSY90, CDCl3): σ ppm 5.58 (d, J=2Hz, H-7), 3.46 (t, J = 1.5, H-3), 3.43 (br s, H-2), 2.49 (m, H-4), 2.27 (dd, J=7.8,7.6Hz, H-5), 2.02 (s, H-21), 2.20–1.60 (overlapping signals of H-11, H-12, H-13, H-14, H-15, H-16 and H-17), 1.85(m,H-1), 1.25 (s,H-19), 1.19 (s, H-18). 13C NMR (75MHz, Assignment by HETCOR): σ 220.0 s(C-6), 180.1 s(C-20), 163.3 d (C-7), 162.2 s (C-8), 97.5 (C-9), 91.9 (C-2), 85.3 t (C-3),65.2 (C-17), 46.1 (C-14), 45.0 (C-5), 39.0 s (C-10), 37.3 (C-13), 34.2 (C-16), 31.1 (C-4), 28.4 (C-15), 33.7 (C-12), 29.5 (C-11), 28.0 (C-1), 25.1(C-21), 23.3 (C-19), 22.4 (C-18)
  • Glasstone , S. 1962 . An Introduction to Electrochemistry , 245 N.Y. Van Nostrand .
  • Tin particles (formed by Mg + Sn++ = Mg++ + Sn) and magnesium particles together form electrolytic cells taking SnCl2 solution as electrolytic medium. Thus, electrons from magnesium [Mg = Mg++ + 2e] are responsible for such reductions
  • Yamamoto , A. , Ookawa , M. and Ikeda , S. 1969 . J. Chem. Soc., Chem. Comm. , : 841
  • Trylik , S. and Wolochowicz , I. 1975 . J. Chem. Soc., Chem. Comm. , : 781

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