Manganese(III)-Mediated Radical Additions of Dimethyl Malonate to Olefins. The Chemoselective Synthesis of Diesters and Lactones

Synlett

Volumn 1996, Issue 5, 1996, Pages 468-470

  Linker, Torsten ^a   Kersten, Berthold ^a   Linker, Ursula ^a   Peters, Karl ^b   Peters, Eva Maria ^b   Von Schnering, Hans Georg ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001849223     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5451     Document Type: Article

References (35)

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20. 4), and concentrated. The excess of dimethyl malonate was removed (100°C, 10 mbar) and the residue was purified by column chromatography. Method B: A mixture of potassium acetate (1.75 g, 18 mmol), manganese(II) acetate tetrahydrate (12.5 mg, 0.05 mmol), dimethyl malonate (6.61 g, 50 mmol), and acetic acid (18 ml) was heated to 75°C under argon atmosphere. After the addition of the olefin (5.00 mmol), solid potassium permanganate (0.3 - 0.4 equiv.) was added in very small portions at 75°C over a period of 4 - 10 h until TLC indicated complete conversion of the olefin. The work up procedure was the same as with method A.
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29. For selected examples see: a) Heiba, E. I.; Dessau, R. M.; Koehl Jr., W. J. J. Am. Chem. Soc. 1968, 90, 5905-5906. b) Fristad, W. E.; Peterson, J. R.; Ernst, A. B. J. Org. Chem. 1985, 50, 3143-3148. c) Allegretti, M.; D'Annibale, A.; Trogolo, C. Tetrahedron 1993, 49, 10705-10714.
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31. For selected examples see: a) Snider, B. B.; Dombroski, M. A. J. Org. Chem. 1987, 52, 5487-5489. b) Oumar-Mahamat, H.; Moustro, C.; Surzur, J.-M.; Bertrand, M. P. J. Org. Chem. 1989, 54, 5684-5688. c) Crombie, B. S.; Redhouse, A. D.; Smith, C.; Wallace, T. W. J. Chem. Soc., Chem. Commun. 1995, 403-404.
32. For selected examples see: a) Snider, B. B.; Dombroski, M. A. J. Org. Chem. 1987, 52, 5487-5489. b) Oumar-Mahamat, H.; Moustro, C.; Surzur, J.-M.; Bertrand, M. P. J. Org. Chem. 1989, 54, 5684-5688. c) Crombie, B. S.; Redhouse, A. D.; Smith, C.; Wallace, T. W. J. Chem. Soc., Chem. Commun. 1995, 403-404.
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35. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre, and are available on request.