References and Notes
- Carmeron , G. G. and Milton , A. J. S. 1976 . J. Chem. Soc. Perkin Trans. II , : 378
- Kharasch , M. S. and Reinmuth , O. 1954 . Grignard reagents of Non-metallic Substances , London : Constable .
- Hauser , C. R. and Humphlett , W. J. 1950 . J. Org. Chem. , 13 : 359
- Sumrell , G. 1954 . J. Org. Chem. , 19 : 817
- To tell between “dephosphorylation” and “dephosphonylation”, we use the term “dephosphonylation” as a limited meaning of P-C bond cleavage in compound including phosphonate group.
- Hong , J. E. , Shin , W. S. , Jang , W. B. and Oh , D. Y. 1996 . J. Org. Chem. , 61 : 99
- Lee , K. and Oh , D. Y. 1989 . Bull. Korean Chem. Soc. , 10 : 613
- Lee , K. and Oh , D. Y. 1991 . Synthesis , : 213
- Lee , K. , Shin , W. S. and Oh , D. Y. 1991 . Synthetic Commun. , 21 : 1657
- Lee , K. and Oh , D. Y. 1991 . Bull. Kor. Chem. Soc. , 12 : 254
- Shin , W. S. , Lee , K. and Oh , D. Y. 1995 . Tetrahedron Lett. , 36 : 281
- In general, the addition of organolithium compounds to aliphatic nitriles are subjected to various side reactions, notably α-deprotonation (ref. 1(d)). We investigated the result on that, and described that in previous report (ref. 4(b)).
- Robinson , G. E. and Vernon , J. M. 1972 . J. Chem. Soc. Perkin Trans. I , : 1277
- In earlier report (ref 3), several experiments with β-keto phosphonate were carried out to investigate the detailed mechanism. When reduction of β-keto phosphonate 5 with LiAlD4 was followed by quenching with dilute H2SO4, the reaction afforded the ketone 6 containing no deuterium. In case of using LiAlH4 and deuterized acid, the reaction gave the ketone 7 involving two deuteriums. Because ketones do not exchange its α-proton rapidly, this two result can be the evidence that hydride attacked the phosphorus atom directly. However in the case of enamine, proton exchange is occured rapidly in hydrolysis step, so above experiment cannot be adapted in this paper. But mechanisms of these two reactions are presumed to be identical.