Reaction of 1-Bromo-1-Nitropropane and Trimethyl Phosphite

Bulletin of the Korean Chemical Society

Volumn 18, Issue 2, 1997, Pages 129-130

  Kim, Kwan Soo ^a   Hurh, Eun Young ^a   Park, Yong Hoon ^a   Park II, Jong ^a   Kim, Sam Sik ^a  

^a Yonsei University   (South Korea)

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Indexed keywords

EID: 0344117752     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (9)

1. Allen, J. F. J. Am. Chem. Soc. 1957, 79, 3071.
2. Fishwick, B. R.; Rowles, D. K.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. I 1986, 1171.
3. Burgess, H.; Donnelly, J. A. Tetrahedron 1991, 47, 111.
4. Erickson, A. S.; Kornblum, N. J. Org. Chem. 1977, 42, 3764.
5. 4P 181.050396, found 181.050541.
6. Less than two equivalents of trimethyl phosphite gave the same product but with lower yield. The ratio of E-and Z-isomers was varied with the reaction conditions and each isomer could not be separated as a pure form because of the rapid isomerization during chromatography. Although the HPLC yield reached 80%, the isolated yield was only 58% maybe because of the partial decomposition of the product during purification.
7. 5PSi: C, 42.44; H, 8.36; N, 4.50 found C, 43.39; H, 8.77; N, 4.63.
8. Joffe, S. L.; Shitkin, V. M.; Khasapov, B. N.; Kashutina, M. L.; Tartakovskii, V. A.; Myagi, M. Y.; Lippmaa, E. T. Izv. Akad. Nauk SSSR. Ser. Khim. 1973, 2146; English transl. p 2100.
9. Colvin, E. W.; Beck, A. K.; Bastani, B.; Seebach, D.; Kai, Y.; J. D. Dunitz, J. D. Helv. Chim. Acta. 1980, 63, 697.