Structure and reactivity of an isolable seven-membered-ring trans-alkene

Brisa Hurlocker; Chunhua Hu; K A Woerpel

doi:10.1002/anie.201410752

Structure and reactivity of an isolable seven-membered-ring trans-alkene

Angew Chem Int Ed Engl. 2015 Mar 27;54(14):4295-8. doi: 10.1002/anie.201410752. Epub 2015 Feb 5.

Authors

Brisa Hurlocker¹, Chunhua Hu, K A Woerpel

Affiliation

¹ Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA).

PMID: 25656271
DOI: 10.1002/anie.201410752

Abstract

The isolation and characterization of a trans-oxasilacycloheptene is reported. Single-crystal X-ray crystallographic studies indicate a high level of strain and deviation from ideal geometry. Reactions with several electrophiles demonstrated the nucleophilicity of the C=C double bond, affording oxasilacycloheptane and tetrahydrofuran products as single diastereomers.

Keywords: alkenes; cycloheptenes; medium-ring compounds; silicon; strained molecules.