Search results

Search for "retro-addition" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Graphical Abstract
PDF
Album
Review
Published 18 May 2021

Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion

  • Rudolf Knorr and
  • Barbara Schmidt

Beilstein J. Org. Chem. 2018, 14, 3018–3024, doi:10.3762/bjoc.14.281

Graphical Abstract
  • fission may also be used to generate different metal derivatives of the nucleofugal anions as equilibrium components. Fluoride-catalyzed, metal-free desilylation admitted carbonyl addition but blocked the retro-addition. Keywords: alkoxide fission; desilylation; fragmentation; retro-addition; reversible
  • and a carbonyl compound (R1)2C=O. Such a C–C fission (retro-addition reaction) can occur already near room temperature (rt) if the nucleofugal carbanion proves to be an electronically stabilized N≡C–CH2– [1] or allylic [2] species or a short-lived equilibrium component [3]. A cleavable alkoxide A1M1
  • blocked by FSiMe3 and hence unsuitable for an analysis of the retro-addition reaction (see Supporting Information File 1). Conclusion (i) The nucleofugal carbanion (α-deprotonated 1) can escape with surprising ease from alkoxides, perhaps with some assistance by a metal cation if present. Conversely
PDF
Album
Supp Info
Full Research Paper
Published 11 Dec 2018
Other Beilstein-Institut Open Science Activities