Work

Examining the silicon‑fluorine gauche effect in 3-fluoro silacyclohexanes

Year: 2025

Type: article

Abstract: Two 3-fluorosilinanes featuring different substitution at silicon were synthesized and their conformations analyzed by NMR and DFT. Based on the results, both compounds prefer a conformation wherein the fluorine atom is oriented equatorial rather than axial, which would have placed the partially negative fluorine (F δ- ) closer in space to partially positive silicon (Si δ+ ). Therefore, the conformational preference of these systems is thought to be controlled primarily by sterics as well as hyperconjugative stabilization (σ C-Si → σ* C-F ). • A synthesis of 3-fluorosilinanes was developed to investigate their conformation. • By NMR, fluorine adopts an equatorial position in the two silinanes investigated. • Hyperconjugation is thought to be an important factor in these systems.

Source: Tetrahedron Letters

DOI: 10.1016/j.tetlet.2025.155902

Authors: K.E. Wier, S.M. Conner, R.F. Berger, G.W. O'Neil

Institution: Western Washington University

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,610

Funders: Foundation for the National Institutes of Health, National Institutes of Health, American Chemical Society Petroleum Research Fund