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![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Improved reactivity of a cyclic 13/15 compound by increased steric demand
Markus Balmer1, Manuel Kapitein, Carsten von Hänisch
1Fachbereich Chemie and Wissenschaftliches Zentrum für Materialwissenschaften (WZMW), Philipps-Universität Marburg, 35032 Marburg, Germany. haenisch@staff.uni-marburg.de.
Abstract:
Herein we present the synthesis and characterization of the new four-membered Ga/P cycle [tBu2GaP(H)SitBu2Ph]2, which shows a cis/trans isomerization at ambient temperatures via a ring opening mechanism. The sterically demanding substituents on the phosphorus (-SitBu2Ph) and gallium (tBu) atoms lead to an unexpected reactivity towards bulky NHC ligands (IMes and IDipp). The resulting Lewis base stabilized monomeric 13/15 compounds feature an unusual binding mode of the carbene ligand. The ring opened state also enables a masked flp reactivity, which is shown by a reaction with the polar multiple bond in Ph-NCO.
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