Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 1999 May 3;38(9):1261-1263.
doi: 10.1002/(SICI)1521-3773(19990503)38:9<1261::AID-ANIE1261>3.0.CO;2-E.

[(Ph)2 (NMe2 )C(OLi)⋅THF]2 : Crystal Structure of the Tetrahedral Intermediate Formed in the Reaction of N,N-Dimethylbenzamide and Phenyllithium

Martin Adler  1 , Michael Marsch  1 , Norma Sbarbati Nudelman  2 , Gernot Boche  1
Affiliations

[(Ph)2 (NMe2 )C(OLi)⋅THF]2 : Crystal Structure of the Tetrahedral Intermediate Formed in the Reaction of N,N-Dimethylbenzamide and Phenyllithium

Martin Adler et al. Angew Chem Int Ed Engl. .

Abstract

Information on the reaction path for the 1,2-eliminiation of LiNMe2 to form benzophenone is provided by the X-ray crystal structure analysis of the tetrahedral adduct [(Ph)2 (NMe2 )C(OLi)⋅THF]2 (a portion of the structure is shown schematically), which is prepared from N,N-dimethylbenzamide and phenyllithium. A N1-Li1 interaction, which is not observed, would lead to loss of the anomeric effect (nN →σ*C-O ) as well as high conformational strain along the C1-N1 bond.

Keywords: Carbonyl compounds; Intermediates; Nucleophilic additions.

PubMed Disclaimer

LinkOut - more resources