189329-47-3Relevant academic research and scientific papers
Regio- and stereoselective addition of methane- and bromomethanesulfonyl bromides to 1-Phenylthiotricyclo[4.1.0.02,7]heptane
Vasin,Kostryukov,Neverov,Razin
scheme or table, p. 624 - 627 (2010/10/04)
1-Phenylthiotricyclo[4.1.0.02,7]heptane reacted with MeSO 2Br and BrCH2SO2Br directly at mixing at 20°C in CH2Cl2 along a ionic (electrophilic with respect to bromine) mechanism affording a product of an anti-stereoselective addition to the central bicyclobutane C1-C7 bond of the norpinane structure. The reaction product contains the exo-oriented sulfonyl group in the geminal position to the SPh substituent. The structure of the adduct with MeSO2Br in a single crystal was determined by XRD analysis. Pleiades Publishing, Ltd., 2010.
Synthesis of Norpinane and Tricyclo[4.1.0.02,7]heptane Derivatives from 1-Phenylthiotricyclo[4.1.0.02,7]heptane
Vasin,Razin,Kostryukov
, p. 1657 - 1666 (2007/10/03)
Radical addition of PhSO2Hlg (Hlg = Cl, Br) to 1-phenylthiotricyclo[4.1.0.02,7]heptane results in endo,syn-stereoselective splitting of the central bicyclobutane C1-C7 bond with formation of norpinane derivatives. The latter readily undergo substitution of the halogen by the action of nucleophiles (H2O, MeONa, PhSNa) and 1,3-dehydrohalogenation to 1-phenylsulfonyl-7-phenylthiotricyclo[4.1.0.02,7]heptane by the action of t-BuOK in THF. The stereoselective endo,syn addition of benzenesulfenyl chloride and benzeneselenol and also addition of benzenethiol in the presence of H2SO4 at the C1-C7 bond follows the Markownikoff rule. Acid-catalyzed hydration and bromohydroxylation with N-bromosuccinimide result in formation of 6-norpinanone derivatives.
