Aldehydes and ketones form intermediate π complexes with the Gilman reagent, Me2CuLi, at low temperatures in tetrahydrofuran

Steven H Bertz; Richard A Hardin; Craig A Ogle

doi:10.1021/ja404105u

Aldehydes and ketones form intermediate π complexes with the Gilman reagent, Me2CuLi, at low temperatures in tetrahydrofuran

J Am Chem Soc. 2013 Jul 3;135(26):9656-8. doi: 10.1021/ja404105u. Epub 2013 Jun 18.

Authors

Steven H Bertz¹, Richard A Hardin, Craig A Ogle

Affiliation

¹ Department of Chemistry, University of North Carolina at Charlotte, Charlotte, North Carolina 28223, USA. sbertz1@uncc.edu

PMID: 23777294
DOI: 10.1021/ja404105u

Abstract

Typical aldehydes and ketones form π complexes with Me2CuLi at low temperatures in tetrahydrofuran. They range in stability from fleeting intermediates at -100 °C to entities that persist up to -20 °C. Three subsequent reaction pathways have been identified.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aldehydes / chemistry*
Copper / chemistry*
Furans / chemistry*
Ketones / chemistry*
Lithium / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Temperature

Substances

Aldehydes
Furans
Ketones
Organometallic Compounds
tetrahydrofuran
Copper
Lithium