Abstract:
In the AdE reaction of RSC1 with 3,3-dimethylbut-l-ene the system MeNO2–LiClO4 serves as an efficient promoter of a 1,2-shift which occurs either simultaneously with the electrophilic addition step (π-route) or as a rearrangement of the initially-formed 1,2-adducts (σ-route) and proceeds in a highly stereoselective fashion.
Document Type:
Article
Language: English
Citation:
A. B. Borisov, I. V. Bodrikov, G. N. Borisova, V. K. Belsky, W. A. Smit, A. I. Lutsenko, “Use of MeNO2–LiClO4 in promoting a 1,2-shift in RSCI electrophilic addition to 3,3-dimethylbut-1-ene: reaction course and stereochemistry”, Mendeleev Commun., 6:2 (1996), 52–53
Linking options:
https://www.mathnet.ru/eng/mendc4910
https://www.mathnet.ru/eng/mendc/v6/i2/p52
This publication is cited in the following 6 articles:
A. V. Borisov, V. K. Osmanov, G. N. Borisova, Zh. V. Matsulevich, G. K. Fukin, “Two directions of heterocyclization in the reactions of dimethyl bicyclo[2.2.2]oct-5-ene-endo-2,endo-3-dicarboxylate with hetarenesulfenyl chlorides”, Russ Chem Bull, 67:3 (2018), 525
A. V. Borisov, V. K. Osmanov, G. N. Borisova, Zh. V. Matsulevich, G. K. Fukin, “Synthesis of condensed sulfur- and nitrogen-containing heterocycles via polar cycloaddition of hetarene sulfenyl chlorides to a C–C multiple bond”, Mendeleev Commun., 19:1 (2009), 49–51
A. V. Borisov, V. K. Belsky, V. K. Osmanov, G. N. Borisova, Zh. V. Matsulevich, “Sulfenyl halides in the synthesis of heterocycles. 3. Interaction of perfluoro-1-ethyl-2-methyl-1-propenyl-iminochloromethanesulfenyl chloride with 1-allyl-2-methoxybenzene”, Chem Heterocycl Compd, 42:10 (2006), 1346
A. V. Borisov, V. K. Belsky, T. V. Goncharova, G. N. Borisova, V. K. Osmanov, Zh. V. Matsulevich, N. G. Frolova, E. D. Savin, “Sulfenyl Halides in the Synthesis of Heterocycles. 2. Cyclization in Reactions of Hetarenesulfenyl Chlorides with 3,3-Dimethyl-1-butene”, Chem Heterocycl Compd, 41:6 (2005), 771
Margarita I. Lazareva, Yury K. Kryschenko, Anthony Hayford, Mark Lovdahl, Ron Caple, William A. Smit, “Controlled one-pot sequence of three AdE reactions as a novel protocol for the synthesis of polyfunctional compounds”, Tetrahedron Letters, 39:10 (1998), 1083
A. B. BORISOV, I. V. BODRIKOV, G. N. BORISOVA, V. K. BEL'SKY, W. A. SMIT, A. I. LUTSENKO, “ChemInform Abstract: Use of MeNO2‐LiClO4 in Promoting a 1,2‐Shift in RSCl Electrophilic Addition to 3,3‐Dimethylbut‐1‐ene: Reaction Course and Stereochemistry.”, ChemInform, 27:35 (1996)
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