135356-98-8Relevant academic research and scientific papers
74. Solvolysis Mechanism of cis- and trans-2-Arylcyclopentyl p-Toluenesulfonates. Subsequent Step in cis-2-Arylcyclopentyl p-Toluenesulfonate Solvolysis
Ronco, G.,Guyon, R.,Villa, P.
, p. 658 - 673 (1988)
The solvolysis of a series of 1-deuteriated, 2-deuteriated, and undeuteriated cis-2-arylcyclopentyl p-toluenesulfonates in HCOOH, AcOH, and EtOH has been studied.We have shown that the classical secondary carbocation arising from substrate ionisation undergoes two concurrent processes, namely kc (direct products formation) and kip (hydrogenium bridged ion formation as tertiary carbocation or products precursor).The intrinsic properties of solvent and the aryl substituent electronic effects only affect the total solvolysis rate and the respective contributions of kc and kip processes.Comparing the observed and calculated kinetic isotope effects of D-C(2) allows one to conclude that no step can be called 'rate-determining step' but that the steps following ionisation have a preponderent effect on the total solvolysis rate.
76. Solvolysis Mechanism of cis- and trans-2-Arylcyclopentyl p-Toluenesulfonates. Subsequent Step in trans-2-Phenylclopentyl p-Toluenesulfonate Solvolysis
Ronco, G.,Guyon, R.,Villa, P.
, p. 674 - 684 (1988)
The solvolysis of the 1-deuteriated, 2-deuteriated, and undeuteriated trans-2-phenylcyclopentyl p-toluenesulfonate in HCOOH, AcOOH, and EtOH has been studied.We have shown that the classical secondary carbocation arising from substrate ionisation undergoes three concurrent processes, namely kc (direct product formation), kip (hydrogenium bridged ion formation as tertiary carbocation or products precursor) and kΔph (phenonium-ion formation as retained product precursor).The kΔpd process contribution increases with solvent ionising power.The kinetic isotope effect of D-C(1) shows, that the steps following ionisation have a preponderant effect on the total solvolysis rate.
Kinetic resolution of (±)-trans- and (±)-cis-2- phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: The key role of the leaving group
Gonzalez-Sabin, Javier,Gotor, Vicente,Rebolledo, Francisca
, p. 481 - 488 (2007/10/03)
Kinetic resolution of (±)-trans- and (±)-cis-2- phenylcyclopentanamine is effectively performed by lipase B from Candida antarctica, (CALB)-catalyzed aminolysis reaction. Whereas reaction between (±)-trans-2-phenylcyclopentanamine and ethyl acetate proceeds with a very high E value (>200) and conversion (50%), the corresponding acetylation of (±)-cis-2-phenylcyclopentanamine happens with low E value (16) and conversion (28%). Nevertheless, this problem is overcome using other acyl donors such as (±)-1-phenylethyl and (±)-cis-2-phenylcyclopentyl methoxyacetates. The influence of the acyl donor on the CALB-catalyzed aminolysis of (±)-cis-2-phenylcyclopentanamine is also studied.
Enzymatic hydrolysis and esterification. Routes to optically pure cyclopentanols
Seemayer, R.,Schneider, M. P.
, p. 171 - 174 (2007/10/02)
Using an esterhydrolase from Pseudomonas sp. (SAM II), a series of optically pure cyclopentanols 1-4 was prepared by enzymatic hydrolysis of their corresponding acetates.Using the same enzyme, these cyclopentanols were esterified by enol esters as acyl do
