Effect of CH/pi interaction on exo/endo selectivity in 1,3-dipolar cycloadditions

Warning

This publication doesn't include Faculty of Economics and Administration. It includes Faculty of Science. Official publication website can be found on muni.cz.
Authors

MELŠA Petr ČAJAN Michal MAZAL Ctibor

Year of publication 2004
Type Article in Proceedings
Conference YoungChem 2004, Book of Abstracts
MU Faculty or unit

Faculty of Science

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:

You are running an old browser version. We recommend updating your browser to its latest version.