References
- Jacobs , T. L. 1949 . Org. React. , 5 : 1 However, it is noteworthy that a recent evaluation of this method reports modest yield (32–55%) for the dehydrohalogenation step;
- Mesnard , D. , Bernadou , F. and Miginiac , L. 1981 . J. Chem. Res. (M) , : 3216
- Ben-Efraim , D. A. 1978 . The Chemistry of the Carbon-Carbon Triple Bond, Part 2 , Edited by: Patai , S. New York : Wiley .
- Newman , M. S. and Wood , L. L. Jr. 1959 . J. Am. Chem. Soc. , 81 : 4300
- Wassilieff , M. W. 1928 . Bull. Soc. Chim. Fr. , 43 : 563 An alternate route to 4 may involve α-chlorination of the starting ketone to give i (seeand reference 1) which is then converted to 4 with a second equivalent of PCl5. However, we have not detected i in our experiments. An authentic sample of i (R = CH3, X = 4-OCH3) was prepared by the method of Kasower, et. al. (Kosower, E. M.; Cole, W. J.; Wu, G.-S.; Cardy, D. E.; Meisters, G. J. Org. Chem. 1963, 28, 630); 1H NMR (300 MHz, CDCl3) 1.73 (3H, d, J = 7 Hz), 3.88 (3H, s), 5.23 (1H, q, J = 7 Hz), 6.96 (2H, d, J = 9 Hz), 8.00 (2H, d, J = 9 Hz).
- For a summary of synthetically useful methods for alkyne formation, see reference 1b.
- Adams , R. , Geissman , T. A. , Baker , B. R. and Teeter , H. M. 1941 . J. Am. Chem. Soc. , 63 : 528
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- Gramatica , P. , Monti , D. and Manitto , P. 1974 . Gazz. Chim. Ital. , 104 : 629
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- Libman , N. M. and Shandybina , O. N. 1984 . Zh. Org. Khim , 20 : 2517