237391-54-7Relevant academic research and scientific papers
Products and mechanism of some halogenation reactions of 1-sulfonyl-substituted tricyclo[4.1.0.02,7]heptanes
Vasin,Petrov,Kalyazin,Razin
experimental part, p. 358 - 367 (2012/06/18)
Reactions of 1-methylsulfonyl- and 1-phenylsulfonyltricyclo[4.1.0.0 2,7]heptanes with iodine, dioxane dibromide, and dichloro-λ3- iodanylbenzene (under irradiation) gave products of stereoselective syn addition of halogen at the C1-C7 central bicyclobutane bond. 7-Methyl-1-phenylsulfonyltricyclo[4.1.0.02,7]- heptane reacted with dioxane dibromide in carbon tetrachloride to produce a mixture of 2-bromo- and 2,3-dibromo- 1-methyl-exo-7-phenylsulfonylnorcaranes at a ratio of 1 : 4 as a result of cleavage of the C1-C2 bicyclobutane bond. 7-Bromo- and 7-methoxycarbonyl-1-phenylsulfonyltricyclo[4.1.0.0 2,7]heptanes take up bromine exclusively at the C1-C 7 central bond with strict syn stereoselectively. The regio- and stereoselectivity of the addition and their relations with the halogen nature were interpreted with account taken of structural specificities of intermediate 6-sulfonyl-substituted 6-norpinanyl radicals determined by ab initio quantumchemical calculations using 6-31G basis set. Pleiades Publishing, Ltd., 2012.
Photochemical reaction of 1-phenylsulfonyltricyclo[4.1.0.02,7]heptane with benzenesulfonyl bromide
Vasin,Kostryukov,Rasin
, p. 1136 - 1142 (2007/10/03)
Phenylsulfonyltricyclo[4.1.0.02,7]heptane reacts with PhSO2Br under UV light to yield the products of sulfobromination and bromination in 3:1 ratio. Both addition processes are highly cis-stereo-selective. The structure of the bromin
