138173-74-7Relevant articles and documents
Carbanionic rearrangements of halomethylenecyclobutanes. The role of the halogen
Du, Zhengming,Haglund, Melissa J.,Pratt, Lauri A.,Erickson, Karen L.
, p. 8880 - 8887 (1998)
The carbanionic ring enlargement of (halomethylene)cyclobutanes to 1- halocyclopentenes has been extended to the fluoro analogues. At 180 °C, 3- hexyl-1-(fluoromethylene)cyclobutane provides better yields of rearranged product than the corresponding chloride, bromide, or iodide. At temperatures Br > Cl, and the fluoride does not react. Experiments with labeled substrates show that, in general, the larger the halide and the higher the reaction temperature, the greater the preference for double migration over Single migration as a mechanistic pathway. The trifluormethyl group is ineffective in promoting anionic rearrangement.
Transition-Metal-Promoted Direct C?H Cyanoalkylation and Cyanoalkoxylation of Internal Alkenes via Radical C?C Bond Cleavage of Cycloketone Oxime Esters
Lou, Jiang,He, Yuan,Li, Yunlong,Yu, Zhengkun
supporting information, p. 3787 - 3799 (2019/07/10)
Transition-metal-catalyzed alkyl-Heck-type cross-coupling of olefinic C?H bonds has been a challenge in the C?H activation area. Herein, we report FeCl3-promoted efficient direct C?H cyanoalkylation of internal alkenes, that is, ketene dithioacetals, with cycloketone oxime esters via radical C?C bond cleavage under the redox-neutral conditions. With CuCl2 as the catalyst under a dioxygen atmosphere direct C?H cyanoalkoxylation of the same internal alkenes was achieved. The cyanoalkylated tetrasubstituted alkene products could be diversely transformed to cyanoalkyl-funtionalized N- and S-heterocyclic compounds. The mechanistic studies have revealed that these C?H cyanoalkylation and cyanoalkoxylation reactions proceed through a radical pathway. (Figure presented.).
A general synthesis of cyclobutanones from olefins and tertiary amides: 3-Hexylcyclobutanone
Schmit,Falmagne,Escudero,Vanlierde,Ghosez
, p. 199 - 199 (2017/06/01)
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