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Angle-strained sila-cycloalkynes.
Wakefield, Herbert; Melvin, Sophia J; Jiang, Jennifer; Kevlishvili, Ilia; Siegler, Maxime A; Craig, Stephen L; Kulik, Heather J; Klausen, Rebekka S.
  • Wakefield H; Department of Chemistry, Johns Hopkins University, 3400 N. Charles St, Baltimore, MD 21218, USA. Klausen@jhu.edu.
  • Melvin SJ; Department of Chemistry, Johns Hopkins University, 3400 N. Charles St, Baltimore, MD 21218, USA. Klausen@jhu.edu.
  • Jiang J; Department of Chemistry, Johns Hopkins University, 3400 N. Charles St, Baltimore, MD 21218, USA. Klausen@jhu.edu.
  • Kevlishvili I; Department of Chemical Engineering, Massachusetts Institute of Technology, 25 Ames St, Cambridge, MA 02139, USA.
  • Siegler MA; Department of Chemistry, Johns Hopkins University, 3400 N. Charles St, Baltimore, MD 21218, USA. Klausen@jhu.edu.
  • Craig SL; Department of Chemistry, Duke University, 124 Science Drive, Box 90354, Durham, NC 27708, USA.
  • Kulik HJ; Department of Chemical Engineering, Massachusetts Institute of Technology, 25 Ames St, Cambridge, MA 02139, USA.
  • Klausen RS; Department of Chemistry, Massachusetts Institute of Technology, Room 18-393, 77 Massachusetts Ave, Cambridge, MA 02139, USA.
Chem Commun (Camb) ; 60(36): 4842-4845, 2024 Apr 30.
Article en En | MEDLINE | ID: mdl-38619444
ABSTRACT
Second row elements in small- and medium-rings modulate strain. Herein we report the synthesis of two novel oligosilyl-containing cycloalkynes that exhibit angle-strain, as observed by X-ray crystallography. However, the angle-strained sila-cyclooctynes are sluggish participants in cycloadditions with benzyl azide. A distortion-interaction model analysis based on density functional theory calculations was performed.