19522-36-2Relevant academic research and scientific papers
Photochemical generation and structure of vinyl radicals
Goumans, Theodorus P. M.,Van Alem, Kaj,Lodder, Gerrit
, p. 435 - 443 (2008)
Photolysis of a series of E or Z stereoisomeric α-R-substituted bromostyrenes (R = CH3, F or CN) in methanol yields E and/ or Z stereoisomeric styrenes, which stem from the corresponding vinyl radicals. The results show that the α-Me vinyl radical is a rapidly equilibrating, bent structure, while the α-F vinyl radical is a stable bent species, in agreement with earlier thermal results. The α-CN vinyl radical is assigned as a rapidly inverting bent and not a linear species from the stereochemical results as a function of temperature. Stereochemical data for the α-C(H)=O system in diethyl ether indicate a stable bent vinyl radical as product forming species. The conclusions are supported by quantum chemical computations. Wiley-VCH Verlag GmbH & Co. KGaA.
Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes
Iakovenko, Roman,Hlavá?, Jan
, p. 440 - 446 (2021/01/28)
Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is
