Theoretical evidence for stereoselective lithiations of 
2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study

Barluenga, José; González, José M.; Llorente, Isidro; Campos, Pedro J.; Rodríguez, Miguel A.; Thiel, Walter

doi:10.1016/S0022-328X(97)00403-8

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study

MPS-Authors

There are no MPG-Authors in the publication available

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Barluenga, J., González, J. M., Llorente, I., Campos, P. J., Rodríguez, M. A., & Thiel, W. (1997). Theoretical evidence for stereoselective lithiations of 2-alkoxy-1,1-diiodo-1-alkenes. An ab initio study. Journal of Organometallic Chemistry, 548(2), 185-189. doi:10.1016/S0022-328X(97)00403-8.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-5CD6-2

Abstract

Ab initio calculations with complete geometry optimization are reported for monomeric Z- and E-2-methoxy-1-iodo-1-lithio-2-phenyl-1-alkenes. All the stationary points are true local minima on the energy surfaces. The structural data of the lithioalkenes show clear-cut evidence for the Li-Phenyl interaction in Z-isomer and the Li-O chelation in E-isomer in gas-phase. Based on the ab initio energies, Li-Phenyl interaction should be less relevant than Li,O chelation. Both effects are absent when coordination by solvent (water) is accounted. Inclusion of solvation by solvent continuum model (IPCM) seems essential to rationalize the experimental results.