189329-89-3

Upstream product

• 189329-48-4 (1R,5S,6S,7R)-7-Benzenesulfonyl-6-bromo-6-phenylsulfanyl-bicyclo[3.1.1]heptane 
• 189329-47-3 (1R,5S,6S,7R)-7-Benzenesulfonyl-6-chloro-6-phenylsulfanyl-bicyclo[3.1.1]heptane 
• 1197-98-4 benzenesulfonyl thiocyanate 
• 2297-65-6 benzenesulfonyl bromide 
• 98-09-9 benzenesulfonyl chloride 
• 1212-08-4 S-Phenyl benzenethiosulfonate 

Relevant academic research and scientific papers

Synthesis of 7-sulfonyl-substituted norpinan-6-ones and -thiones from 1-bromotricyclo[4.1.0.02,7]heptane

1-Bromotricyclo[4.1.0.02,7]heptane reacted with benzene- and methanesulfonyl thiocyanates in benzene at 20°C via anti addition to the central C1-C7 bicyclobutane bond with formation of 6-endo-bromo-6-exo-thiocyanato-7-syn-

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.