89279-83-4

Basic information

• Product Name: (+/-)-(2S,S)-endo-bicyclo<2.2.1>hept-5-enyl-p-tolylsulfoxide
• Synonyms: (+/-)-(2S,S)-endo-bicyclo<2.2.1>hept-5-enyl-p-tolylsulfoxide
• CAS NO: 89279-83-4
• Molecular Weight: 232.346
• Mol File: 89279-83-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+/-)-(2S,S)-endo-bicyclo<2.2.1>hept-5-enyl-p-tolylsulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-(2S,S)-endo-bicyclo<2.2.1>hept-5-enyl-p-tolylsulfoxide(89279-83-4)
• EPA Substance Registry System: (+/-)-(2S,S)-endo-bicyclo<2.2.1>hept-5-enyl-p-tolylsulfoxide(89279-83-4)

Safety Data

• Hazardous Substances Data: 89279-83-4(Hazardous Substances Data)

Upstream product

• 54828-68-1 (R)-p-tolyl vinyl sulfoxide 
• 542-92-7 cyclopenta-1,3-diene 
• 71841-93-5 (-)-S-p-tolyl-S-vinyl-N-phthaloimidosulfoximine 
• 71841-82-2 S-p-tolyl-S-vinyl-N-phthalimidosulphoximide 
• 89279-74-3 (+/-)-(2S,R)-S-endo-bicyclo<2.2.1>hept-5-enyl-N-phthalimido-S-p-tolylsulfoximine 
• 27328-17-2 (S)-(-)-p-tolyl vinyl sulfoxide 

Downstream Products

• 89294-00-8 (1S,4S,5S)-5-p-Tolylsulfanyl-bicyclo[2.2.1]hept-2-ene 
• 89294-00-8 (1S,4S,5R)-5-p-Tolylsulfanyl-bicyclo[2.2.1]hept-2-ene 

Relevant articles and documents

Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate

p-Tolyl vinyl sulfoxide has been efficiently activated for the Diles-Alder reactions by transformation into a sulfonium salt 3a or by addition of TMSOTf.Very high diastereomeric excesses have been achieved (>98percent) at -20 deg C in many cases.Best results have been obtained with cyclopentadiene, furan and 2,3-dimethyl-1,3-butadiene.In this way enantiomerically pure oxanorbornenone 19a has been prepared.The reaction mechanism is briefly discussed.

INVESTIGATION OF A CHIRAL MASKED KETENE SYNTHON. SYNTHESIS OF THE (+)-(1R,4R) and (-)-(1S,4S) ENANTIOMERS OF DEHYDRONORCAMPHOR

The Diels-Alder reaction between (+)-(R)-p-tolyl vinyl sulphoxide and cyclopentadiene gives four separable diastereoisomers.The two most abundant were transformed by a two-step procedure into the two enantiomers of dehydronorcamphor (bicyclohept-5-