| Autor: |
Inouye, Yoshinobu, Mitsuya, Morihiro, Tokuhisa, Kenji, Kakisawa, Hiroshi |
| Zdroj: |
Bulletin of the Chemical Society of Japan; November 1990, Vol. 63 Issue: 11 p3300-3306, 7p |
| Abstrakt: |
The 1,3-dipolar cycloaddition of nitrile oxides to 2-X-bicyclo[2.2.2]oct-5-enes (X=O, NMe, S, SO2) were investigated together with acyclic and alicyclic analogues. The regioselectivity in an exo-attack was controlled by the heteroatom present at an allylic position —a remote attack was predominant in the cases of O and SO2but a vicinal attack in those of NMe and S— and the results were rationalized from the electronic nature of the heteroatom, X. In an endo-attack, a remote attack was observed in every case and the dipole-dipole repulsion between X and the oxygen of the nitrile oxide was considered to be a predominant factor. The steric environment around the heteroatom controled the facial-selectivity. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
|
