References
- Clive , D. L. J. 1978 . Tetrahedron , 34 : 1049 For a detailed outline of the scope and limitations of selen-oxide eliminations, see
- Reich , H. J. 1979 . Accts. Chem. Res. , 12 : 22
- Reich , H. J. , Renga , J. M. and Reich , I. L. 1974 . J. Org. Chem. , 39 : 2133
- Reich , H. J. and Renga , J. M. 1975 . J. Org. Chem. , 40 : 3313
- Reich , H. J. and Shah , S. K. 1977 . J. Amer. Chem. Soc. , 99 : 263
- Reich , H. J. , Renga , J. M. and Reich , I. L. 1975 . J. Amer. Chem. Soc. , 97 : 5434
- A number of acyclic 2-phenylselenenylenones have been prepared via propargyl selenoxide rearrangements (ref. 2c). This methodology is, of course, not applicable in the preparation of cyclic 2-phenylselenenylenones
- In large scale reaction cooling in an ice bath may be necessary
- Apparently in progesterone, 9, enolization of the 20-ketone is totally suppressed by pyridine, such that none of the 17- or 21-phenylselenenyl derivatives are produced (see ref. 6)
- Sharpless , K. B. , Lauer , R. F. and Teranishi , A. Y. 1973 . J. Amer. Chem. Soc. , 95 : 6137
- Liotta , D. and Zima , G. 1978 . Tetrahedron Lett. , : 4977 A Markovnikov addition of PhSeCl is expected. See
- Corey , E. J. and Fraenkel , G. 1953 . J. Amer. Chem. Soc. , 75 : 1168 For an example involving pyridine in a Michael addition, see
- Liotta , D. , Paty , P. B. , Johnston , J. and Zima , G. 1978 . Tetrahedron Lett. , : 5091 For a recent example involving the generation of an enolate via the Michael addition of a nucleophilic initiator, see
- Besides starting material, the only observable product in this reaction is 6-phenylselenenylcyclohexenone