Related Experiment Video
Updated: Jan 19, 2026
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism
Jens Weweler1, Sara L Younas1, Jan Streuff1
1Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104, Freiburg im Breisgau, Germany.
Abstract:
A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C-C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.
Related Concept Videos
14:22Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
01:09Radical Chain-Growth Polymerization: Mechanism
06:19Palladium-Catalyzed Cross Coupling
This experiment will demonstrate the concept of a palladium-catalyzed cross coupling. The set-up of a typical Pd-catalyzed cross coupling reaction will be illustrated. Pd-catalyzed cross coupling reactions have had a profound effect on how synthetic chemists create molecules. These reactions have enabled chemists to construct bonds in new and more efficient ways. Such reactions have found widespread...
01:23Mechanical Ventilation III: Noninvasive Ventilation
Noninvasive Positive-Pressure Ventilation...
01:21Mechanism of Breathing III: The Accessory Muscles
The respiratory system is a complex network that relies on primary respiratory muscles like the diaphragm, but also involves accessory muscles to enhance lung expansion and airflow during both inhalation and exhalation.
Enhancing Inhalation with Accessory Muscles:
Accessory muscles such as the sternocleidomastoid, scalene, intercostal, and abdominal muscles are crucial when additional respiratory effort is required, such as during deep...
01:17Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...