35188-27-3Relevant academic research and scientific papers
Reactions of Cyclohexane Derivatives in Superacids
Dean, Christopher,Whittaker, David
, p. 1541 - 1543 (2007/10/02)
The reactions of menthol with FSO3H-SO2 and neomenthyl chloride with SbF5-SO2ClF follow different routes.The first yields a substituted cyclopentyl cation and the second a substituted cyclohexyl cation.Experiments on substituted cyclohexyl chlorides show that replacement of all the hydrogen atoms on the next but one carbon atom to the reaction centre blocks formation of a carbocation.It is suggested that ionisation of an equatorial chlorine atom takes place with assistance from an intramolecular electronic interaction, forming the methyl cyclopentyl carbocation in a synchronous process, rather than stepwise via the cyclohexyl carbocation.Reasons for contrasting behaviour in solvolytic reactions are discussed.
13C- and 1H-NMR Shielding Effects in Aliphatic gauche/trans Fragments
Schneider, Hans-Joerg,Buchheit, Ulrich,Hoppen, Volker,Schmidt, Guenther
, p. 321 - 326 (2007/10/02)
On the basis of improved calculation models, of new NMR measurements with bicycloheptyl and cyclohexyl compounds, and of literature data it is shown that classical mechanisms of sterically induces charge polarizations, of linear electric field, and
Carbon-13 magnetic resonance: hydrogen involvement in γ-anti substituent effects
Forrest, T. P.,Thiel, J.
, p. 2870 - 2875 (2007/10/02)
Chemical shifts have been determined for the carbons in a series of 3,3-dimethylcyclohexyl derivatives, (substituent = H, CH3, NH2, OH, Cl, Br, I).Comparison of the γ-anti substituent effects at carbons 3 and 5 indicates that presence of axial protons on these carbons causes increased shielding by all of the above substituents.The shielding by γ-anti substituents is decreased by the replacement of either the α or γ protons by methyl groups; the extent of the decrease is dependent upon the substituent and upon the position of the hydrogen which is replaced.
