40960-90-5

Basic information

• Product Name: 4a-phenyl 3a-tosyloxy bicyclo(4.4.0)decane
• CAS NO: 40960-90-5
• Molecular Weight: 384.54
• Mol File: 40960-90-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4a-phenyl 3a-tosyloxy bicyclo(4.4.0)decane(CAS DataBase Reference)
• NIST Chemistry Reference: 4a-phenyl 3a-tosyloxy bicyclo(4.4.0)decane(40960-90-5)
• EPA Substance Registry System: 4a-phenyl 3a-tosyloxy bicyclo(4.4.0)decane(40960-90-5)

Safety Data

• Hazardous Substances Data: 40960-90-5(Hazardous Substances Data)

Upstream product

• 40960-89-2 (3ax)-hydroxy-(4ax)-phenylbicyclo<4.4.0>decane 
• 98-59-9 p-toluenesulfonyl chloride 
• 40960-90-5 4a-phenyl 3a-tosyloxy bicyclo(4.4.0)decane 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 19295-16-0 (+/-)-6-phenyl-(4ar,8at)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene 
• 92609-39-7 bicyclo<4.3.0>nonyl phenylcarbinol-3 trans 
• 75479-70-8 (4aR,6S,8aS)-6-Phenyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene 
• 40960-89-2 (3ax)-hydroxy-(4ax)-phenylbicyclo<4.4.0>decane 
• 75479-70-8 (4aS,6S,8aR)-6-Phenyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene 
• 40960-90-5 3(e)-Phenyl-trans-decalin-2(e)-tosylat 

Relevant articles and documents

Parallelism Between Nucleophilically Solvent-Assisted and Phenyl-Assisted Reactions. Possible Existence of Nucleophilically β-Phenyl-Solvated Ion Pairs

Solvolysis rate constants in MeOH and t-BuOH are compared for β-methyl and β-phenyl derivatives of two cycloalkyl systems.It appears that the β-phenyl derivatives solvolyse at the same rate as the β-methyl ones.The lack of deceleration is attributed to phenyl assistance.It is established by configurational analysis of the reaction products, that those products which necessarily originate from a cationic species are the most abundant ones.It is suggested that these reactions could proceed through ion-pair intermediates, which are nucleophilically solvated by phenyl or by the solvent.A parallel between phenyl assistance and 'SN2 (intermediate)' mechanism, suggested by Bentley and Schleyer, is drawn.

CONFORMATION ET REACTIVITE DE DERIVES (4.n.0) BICYCLIQUES A JONCTION trans-XXVII. TRIFLUOROETHANOLYSE DU TOSYLATE DE PHENYL-4a BICYCLO (4.4.0) DECANYLE-3a TRANS. IMPORTANCE DE LA COPLANEITE DES GROUPES C6H5 ET OTs POUR L'ASSISTANCE DU PHENYLE.

The reaction products from the trifluoroethanolysis of trans-fused 4a-phenyl 3a-tosyloxy bicyclo(4.4.0)decane 2 have been investigated and compared with the data previously obtained for trans-fused 4a-phenyl 3a-tosyloxy bicyclo(4.2.0)octane 1.This comparison provides strong evidence that an aryl-assisted pathway is involved in the ionisation of tosylate 2, the assisted rate being 25 times that of the competing unassisted pathway.A comparative study of the solvolytic rates in the case of several similar tosylates (differently substituted and belonging to the (4.4.0) and (4.2.0) series) allowed us to conclude in favour of phenyl-assisted ionisation process, in the case of trifluoroethanolysis of tosylate 1, though the acceleration factor is then only 11.The fact that the ratio of reaction through the assisted pathway is lower for tosylate 1 than for tosylate 2 has been attributed to a less rigorous parallelism of the C-C6H5 and C-OTs bonds implied in the formation of the bridged ion for compound 1.