| Original language | English (US) |
|---|---|
| Pages (from-to) | 1191-1192 |
| Number of pages | 2 |
| Journal | Chemical Communications (London) |
| Issue number | 22 |
| DOIs | |
| State | Published - 1967 |
Funding
The slightly exceptional behaviour of the cyclo- pentyl compound is not understood at present. TABLE 31P Chemical shifts of [Ph,PR]Br and their correspondiqy ylids R methyl . . ethyl . . n-propyl . . n-butyl . . n-hexyl . . 2-propyl . . 3-pentyl . . 3-hexyl . . cyclopent yl cyclohexyl . . 2-butyl . . < (P*P.m.) - 22.7 - 26.2 - 24.1 - 24.0 - 24.4 - 30.9 - 30.2 - 30.1 - 30.3 - 30.7 - 26.6 aylid (P.P-nl.) - 20.3 - 14.6 - 12.2 - 12.6 - 12.2 - 11.3 - 10.5 - 10.9 - 10.7 - 4.8 - 6.4 sylid- sealt + 2.4 + 11-6 +11*9 + 11.4 + 12.2 + 19.6 + 19.7 + 19.2 + 19.6 + 25.9 + 20.2 These results are to be contrasted with the air- stable ylids, whose 31P chemical shifts are only slightly different from those of their respective phosphonium salts.1 Therefore, as one expects, the air-sensitive ylids shield phosphorus better than those ylids which have the negative charge somewhat delocalized. We thank the National Science Foundation for support of this work and for an Undergraduate Research Participation Award (T. J.M.) . (Received, October loth, 1967; Corn. 1085.) 1 A. W. Johnson, “Ylid Chemistry”, Academic Press, 1966, pp. 76-79. E. J. Corey and M. Chaykovsky, J . Amer. Chem. Soc., 1962,84,866. S. 0. Grim, W. McFarlane, E. F. Davidoff, and T. J. Marks, J . Plzys. Chem., 1966,70, 581.
ASJC Scopus subject areas
- General Chemistry