References
- Tennant , G. 1979 . “Comprehensive Organic Chemistry,” , Edited by: Sutherland , I. O. Vol. 2 , 455 Oxford : Pergamon Press .
- Kolbah , D. and Koruncev , D. 1967 . “Methoden der Organischen Chemie,” , Vol. 10 , 91 Stuttgart : Georg Thiemc Verlag . (Houben-Weyl) Pt. 2
- Further applications of this methodology to similar systems where use of hydrazine is not feasible are currently under investigation
- Love , B. E. and Tsai , L. 1992 . Synth. Commun. , 22 : 165
- Rawlinson , D. J. and Sosnovsky , G. 1972 . Synthesis , : 1
- Sosnovsky , G. and Lawesson , S.-O. 1964 . Angew. Chem., Int. Ed. Engl. , 3 : 269
- Meyer , R. and Pillon , D. U.S. Patent 2,870,206 . For some representative examples, see:
- 1960 . Chem. Abstr. , 54 : 1453i
- Kume , H. , Kawasaki , K. and Maekawa , T. Jpn. Kokai Tokkyo Koho 79,125,629 . (Otsuka Chemical Co., Ltd.)
- 1980 . Chem. Abstr. , 92 : 110681e
- Jpn: Kokai Tokkyo Koho 80,145,184 . Toyo Soda Mfg. Co., Ltd.
- 1981 . Chem. Abstr. , 94 : 129501j
- Hayashi , H. , Somei , J. and Okazaki , T. 1988 . Appl. Catal. , 41 : 213 and references given therein
- Hayashi , H. , Kainoh , A. , Katayama , M. , Kawasaki , K. and Okazaki , T. 1976 . Ind. Eng. PRD , 15 : 299 and references given therein
- Hayashi , H. , Mori , M. , Shigemoto , N. and Okazaki , T. 1978 . Ind. Eng. PRD , 17 : 128 and references given therein
- Kauffmann , T. , Albrecht , J. , Berger , D. and Legler , J. 1967 . Angew. Chem., Int. Ed. Engl. , 6 : 633
- Kauffmann , T. and Berger , D. 1968 . Chem. Ber. , 101 : 3022
- Wessjohann , L. , McGaffin , G. and de Meijere , A. 1989 . Synthesis , : 359
- Büchner , W. , Schliebs , R. , Winter , G. and Büichel , K. H. 1989 . “Industrial Inorganic Chemistry,” , 48 – 50 . New York : VCH Publishers .
- Azines were characterized by NMR and capillary GC by which they were readily distinguished from the corresponding ketones and imines. In many instances the products were compared with (and found to be identical to) authentic samples prepared by reaction of ketones with hydrazine.
- Purification procedures were not optimized. As the crude products were typically greater than 80% pure (by GC), we believe further work would improve the yields of purified products.
- Analysis calculated for C16H14Cl2N2 C, 62.97, H, 4.62, N, 9.18. Found: C, 62.76, H, 4.64, N, 9.08. 1H NMR(CDCl3): 7.5–7.45 (m, 2H), 7.43–7.40 (m, 2H), 7.35–7.30 (m, 4H), 2.26 (s, 6H), 13C NMR(CDCl3): 158.2, 139.0, 132.0, 129.8, 129.7, 129.6, 19.1
- Blount , E. R. , Eager , V. W. and Gofstein , R. M. 1946 . J. Am. Chem. Soc. , 68 1983
- Gouvemeur , P. J. L. and Mulangala , J. M. 1977 . Bull. Soc. Chim. Belg. , 86 : 699
- Malament , D. S. and McBride , J. M. 1970 . J. Am. Chem. Soc. , 92 : 4586
- Scheppele , S. F. , Rapp , W. H. , Miller , D. W. , Wright , D. and Marriott , T. 1972 . J. Am. Chem. Soc. , 94 : 539
- Cohen , S. G. , Groszos , S. J. and Sparrow , D. B. 1950 . J. Am. Chem. Soc. , 72 : 3947
- This product was found to be a mixture of two stereoisomers in a ratio of approximately 3:1. The same ratio of stereoisomers was observed in authentic material prepared by reaction of 3-methyl-2-butanone with hydrazine
- Fleming , I. and Harley-Mason , J. 1961 . J. Chem. Soc. , : 5560
- Amal , E. , Elguero , J. , Jacquier , R. , Marzin , C. and Wylde , J. 1965 . Bull. Soc. Chim. Fr. , : 877
- Flegontov , S. A. , Titova , Z. S. , Vul'fson , S. G. , Savin , V. I. and Kitaev , Y. P. 1977 . Izv. Akad. Nauk SSSR, Ser. Khim. , : 1996
- Abelt , C. J. and Pleier , J. M. 1989 . J. Am. Chem. Soc. , 111 : 1795
- Baird , W. and Wilson , F. J. 1927 . J. Chem. Soc. , : 2116
- Duismann , W. , Beckhaus , H.-D. and Rüchardt , C. 1974 . Liebigs Ann. Chem. , : 1348
- Elguero , J. , Jacquier , R. and Marzin , C. 1968 . Bull. Soc. Chim. Fr. , : 713