50848-69-6Relevant academic research and scientific papers
Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp3)-C(sp2) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes
Ge, Jing-Jie,Yao, Chuan-Zhi,Wang, Mei-Mei,Zheng, Hong-Xing,Kang, Yan-Biao,Li, Yadong
, p. 228 - 231 (2016)
A transition-metal-free deacylative C(sp3)-C(sp2) bond cleavage for the synthetically practical oxidative amination of ketones and aldehydes to nitriles is first described, using cheap and commercially abundant NaNO2 as the oxidant and the nitrogen source. Various nitriles bearing aryl, heteroaryl, alkyl, and alkenyl groups could be smoothly obtained from ketones and aldehydes in high yields, avoiding highly toxic cyanides or transition metals.
Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
Gaunt,Yu,Spencer
, p. 1844 - 1845 (2007/10/03)
The allylic hydrogen is found to have a dramatic effect on the regioselectivity of the Wacker oxidation, leading to the postulation that an agostic hydrogen or enyl (σ + π) complex helps to stabilise the key intermediate.
