189329-46-2

Usage

Uses

Used in Organic Synthesis:
(1R,5S,7R)-7-Benzenesulfonyl-6,6-bis-phenylsulfanyl-bicyclo[3.1.1]heptane is used as a key intermediate in organic synthesis for the development of new compounds and materials. Its unique structural features and functional groups enable it to participate in a variety of chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In pharmaceutical research, (1R,5S,7R)-7-Benzenesulfonyl-6,6-bis-phenylsulfanyl-bicyclo[3.1.1]heptane is used as a potential candidate for the development of new drugs. Its specific properties, such as reactivity and stability, can be investigated and optimized for medicinal applications, potentially leading to the discovery of novel therapeutic agents.
Used in Material Science:
(1R,5S,7R)-7-Benzenesulfonyl-6,6-bis-phenylsulfanyl-bicyclo[3.1.1]heptane is also utilized in material science for the design and synthesis of new materials with unique properties. Its functional groups and structural features can be harnessed to create materials with specific characteristics, such as improved stability, reactivity, or other desirable properties, for use in various industries.

Upstream product

• 930-69-8 sodium thiophenolate 
• 189329-48-4 (1R,5S,6S,7R)-7-Benzenesulfonyl-6-bromo-6-phenylsulfanyl-bicyclo[3.1.1]heptane 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 2297-65-6 benzenesulfonyl bromide 

Relevant academic research and scientific papers

Regio- and stereoselective addition of methane- and bromomethanesulfonyl bromides to 1-Phenylthiotricyclo[4.1.0.02,7]heptane

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

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.