Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart ˙ New York A Facile and Selective Synthetic Method for the Preparation of Aromatic Dialdehydes from Diesters via the Amine-Modified SMEAH Reduction System Kazutake Hagiya*, Sunao Mitsui, Hiroaki TaguchiChemical Research Laboratory, Toyo Kasei Kogyo Co., Ltd., 2900 Sone, Takasago, Hyogo 676-0082, JapanFax: +81(794)477180; e-Mail: kazutake-hagiya@toyokasei-kogyo.co.jp; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A new reduction system employing N-methylpiperazine-modified sodium bis(2-methoxyethoxy)aluminum hydride (NMP-SMEAH) for the conversion of aromatic diesters to dialdehydes is described. The method is plain and efficient, and can be carried out under mild and operationally simple conditions applicable for large scale productions. Key words aldehydes - amines - esters - hydrides - reductions Volltext Referenzen References 1 Nagayama K. Shimizu I. Yamamoto A. Bull. Chem. Soc. Jpn. 2001, 74: 803 2 Brown HC. Rao BCS. J. Am. Chem. Soc. 1958, 80: 5377 3 Comprehensive Organic Synthesis Vol. 8: Trost BM. Pergamon; Oxford: 1991. p.259-305 4 Muraki M. Mukaiyama T. Chem. Lett. 1975, 215 5 Zakharkin LI. Khorlina IM. Tetrahedron Lett. 1962, 619 6 Cha JS. Kwon SS. J. Org. Chem. 1987, 57: 5487 7a Weissman PM. Brown HC. J. Org. Chem. 1966, 31: 283 7b Zlatiodsky P. Helv. Chim. Acta 1994, 77: 150 8 Zakharkin LI. Gavrilenko VV. Maslin DN. Khorlina IM. Tetrahedron Lett. 1963, 29: 2087 9 Yoon NM. Ahn JH. An DK. Shon YS. J. Org. Chem. 1993, 58: 1941 10 Kanazawa R. Tokoroyama T. Synthesis 1976, 527 11 Abe T. Haga T. Negi S. Morita Y. Takayanagi K. Hamamura K. Tetrahedron 2001, 57: 2701 12 Teshima S, and Asako Y. inventors; Jpn. Kokai Tokkyo Koho JP 2001031598. 2001 13 Konishi K, Matsuoka M, and Kitao T. inventors; Jpn. Kokai Tokkyo Koho JP 49050020. 14 Gruetzmacher GD. inventors; U. S. Pat. US 4567048. 1986 15 Sanada K, Kawai S, and Endo T. inventors; Jpn. Kokai Tokkyo Koho JP 06135936. 16 Adamczyk M. Rajarathnam E. Tetrahedron: Asymmetry 1998, 9: 3919 17 Novikova TS. Barashkov NN. Yassar A. Hmyene M. Ferraris JP. Synth. Met. 1996, 83: 47 18 Taussig PR, and Storms PW. inventors; U. S. Pat. US 3448156. 1969 19 Matsuoka M. Ishisaka M. Kitao T. Konishi K. Nippon Kagaku Kaishi 1974, 3: 603 20 Teshima S, Konishi M, Tariji K, Asako Y, and Miki S. inventors; Eur. Pat. EP 995734. 21 White RL. Spenser ID. J. Am. Chem. Soc. 1982, 104: 4934
