260358-65-4

Basic information

• Product Name: (+/-)-5-(p-toluenesulfonyl)bicyclo[3.3.1]non-2-en-9-one
• Synonyms: (+/-)-5-(p-toluenesulfonyl)bicyclo[3.3.1]non-2-en-9-one
• CAS NO: 260358-65-4
• Molecular Weight: 290.383
• Mol File: 260358-65-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+/-)-5-(p-toluenesulfonyl)bicyclo[3.3.1]non-2-en-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-5-(p-toluenesulfonyl)bicyclo[3.3.1]non-2-en-9-one(260358-65-4)
• EPA Substance Registry System: (+/-)-5-(p-toluenesulfonyl)bicyclo[3.3.1]non-2-en-9-one(260358-65-4)

Safety Data

• Hazardous Substances Data: 260358-65-4(Hazardous Substances Data)

Upstream product

• 104871-67-2 (R)-2-(p-tolylsulfinyl)-1-cyclohexanone 
• 14195-09-6 2-tosylcyclohexanone 
• 260358-64-3 (+/-)-2-allyl-2-(p-toluenesulfonyl)cyclohexanone 

Relevant articles and documents

Free-radical cyclization of enantiomerically enriched 2-p-tolylthio derivatives of 2-allylcyclohexanones with Mn(III): Asymmetric synthesis of bridged bicyclic ketones and thiochroman-3-ones

Mn(III)-based oxidative intramolecular cyclization of enantiomerically enriched 2-allyl-2-(p-tolylsulfonyl)-cyclohexanone 4 and 2-allyl-2-(p- tolylsulfenyl)cyclohexanone 9 are reported. The observed chemoselectivity (reaction on the allylic double bond yielding bridged bicyclic ketones vs. reaction on the aromatic ring of the p-tolyl group affording thiochroman-3- ones) depends on the sulfur function (sulfone or thioether, respectively), which determines the electronic density of the p-tolyl ring and the conformational preferences of the starting compounds. The nature of the substituent at C-2 is related to the endo/exo selectivity of the cyclization as well as the regioselectivity in the formation of the enones. (C) 1999 Published by Elsevier Science Ltd.