189330-04-9

Basic information

• Product Name: (1R,5S,6R,7S)-7-Benzenesulfonyl-6-methoxy-6-phenylsulfanyl-bicyclo[3.1.1]heptane
• Synonyms: (1R,5S,6R,7S)-7-Benzenesulfonyl-6-methoxy-6-phenylsulfanyl-bicyclo[3.1.1]heptane
• CAS NO: 189330-04-9
• Molecular Weight: 374.525
• Mol File: 189330-04-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,5S,6R,7S)-7-Benzenesulfonyl-6-methoxy-6-phenylsulfanyl-bicyclo[3.1.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,5S,6R,7S)-7-Benzenesulfonyl-6-methoxy-6-phenylsulfanyl-bicyclo[3.1.1]heptane(189330-04-9)
• EPA Substance Registry System: (1R,5S,6R,7S)-7-Benzenesulfonyl-6-methoxy-6-phenylsulfanyl-bicyclo[3.1.1]heptane(189330-04-9)

Safety Data

• Hazardous Substances Data: 189330-04-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 189329-47-3 (1R,5S,6S,7R)-7-Benzenesulfonyl-6-chloro-6-phenylsulfanyl-bicyclo[3.1.1]heptane 
• 189329-48-4 (1R,5S,6S,7R)-7-Benzenesulfonyl-6-bromo-6-phenylsulfanyl-bicyclo[3.1.1]heptane 
• 2297-65-6 benzenesulfonyl bromide 
• 98-09-9 benzenesulfonyl chloride 
• 1212-08-4 S-Phenyl benzenethiosulfonate 

Relevant articles and documents

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.