Effect of CH/pi interaction on exo/endo selectivity in 1,3-dipolar cycloadditions
| Authors | |
|---|---|
| Year of publication | 2004 |
| Type | Article in Proceedings |
| Conference | YoungChem 2004, Book of Abstracts |
| MU Faculty or unit | |
| Citation | |
| Web | http://www.youngchem.com/book.pdf |
| Field | Organic chemistry |
| Keywords | 1;3-dipolar cycloaddition; methylene lactones |
| Description | In order to prove our assumption about the role of CH/pi interaction in preferential formation of exo-isomers, we varied proton affinity of the aromatic ring of 1,3-dipolar nitril ylide reagent introducing para-substituents. Indeed the reactions of 1a with such substituted nitrile ylides yielding mixtures of diastereomers exo-2 and endo-2 showed that the amounts of endo-adducts increased with increasing electron withdrawing character of the substituents Z. |
| Related projects: |