Synlett, Inhaltsverzeichnis LETTER © Georg Thieme Verlag Stuttgart · New York Deoxygenation of Aldehydes and Ketones Using Dichloro Bis(1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato) Zirconium(IV) Heshmatollah Alinezhad*, Mahmood Tajbakhsh*, Fatemeh SalehianDepartment of Chemistry, Mazandaran University, Babolsar, IranFax: +98(112)5242002; e-Mail: heshmat@umz.ac.ir; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Saturated aldehydes and ketones are converted via their p-toluenesulfonyl hydrazones to the corresponding alkanes using dichloro bis(1,4-diazabicyclo[2.2.2]octane)(tetrahydroborato) zirconium(IV) (ZrBDC). The reactions were performed in DMF-sulfolane at 110 °C and gave the corresponding alkanes in high yields. Regioselectivity in the reduction of α,β-unsaturated carbonyl groups was also observed. Key words ZrBDC - tosylhydrazones - reduction - carbonyl compounds - alkanes Volltext Referenzen References 1 Mitchell RH. Lia YH. Tetrahedron Lett. 1980, 2637 2a Lau CK. Dufresne C. Belanger PC. Pietre S. Kim J. J. Org. Chem. 1986, 51: 3038 2b Srikrishna A. Viswajanani R. Sattigeri JA. Yelamaggad CV. Synlett 1995, 93 2c Srikrishna A. Viswajanani R. Sattigeri JA. Yelamaggad CV. Tetrahedron Lett. 1995, 36: 2347 3 Hatano B. Tagaya H. Tetrahedron Lett. 2003, 6331 4a Beh HM. Vanderslice CW. Spehar A. J. Org. Chem. 1969, 34: 3923 4b Hutchins RO. Hoke D. Keogh J. Koharski D. Tetrahedron Lett. 1969, 3495 5a Jacobus J. J. Chem. Soc., Chem. Commun. 1970, 338 5b Maryanoff BE. Milewski CA. J. Chem. Soc., Chem. Commun. 1971, 1097 6a Minlon H. J. Am. Chem. Soc. 1948, 70: 2802 6b Furrow ME. Myers AG. J. Am. Chem. Soc. 2004, 126: 5436 7 Caglioti SL. Tetrahedron 1966, 22: 487 8a Hutchins RO. Milewski G. Maryanoff B. J. Am. Chem. Soc. 1973, 95: 3662 8b Hutchins RO. Kacher M. Rua L. J. Org. Chem. 1975, 40: 923 9 Lau K. Dufresne C. Belanger C. Pietre S. Scheigetz J. J. Org. Chem. 1986, 51: 3038 10 Kim S. Oh CH. Ko JS. Ahn KH. Kin YJ. J. Org. Chem. 1985, 50: 1927 11 Marks TJ. Kolb JR. Chem. Rev. 1977, 77: 263 12a Firouzabadi H. Iranpoor N. Alinezhad H. Synth. Commun. 2002, 32: 3586 12b Firouzabadi H. Iranpoor N. Alinezhad H. Bull. Chem. Soc. Jpn. 2003, 76: 143 13 Meskens FA. Synthesis 1981, 501