14856-64-5Relevant articles and documents
A greener and efficient access to substituted four- and six-membered sulfur-bearing heterocycles
Parisi, Giovanna,Degennaro, Leonardo,Carlucci, Claudia,De Candia, Modesto,Mastrorilli, Piero,Roller, Alexander,Holzer, Wolfgang,Altomare, Cosimo Damiano,Pace, Vittorio,Luisi, Renzo
, p. 5000 - 5015 (2017/07/11)
The regioselective functionalization of four- and six-membered cyclic sulfones was investigated using a lithiation/electrophile trapping strategy. The protocol features an interesting eco-compatibility profile because of the use of 2-MeTHF as a solvent (more eco-friendly than other organic solvents) and n-hexyllithium as a lithiating agent safer than other alkyllithium compounds. Several derivatives were prepared with different stereochemistry and substitution patterns. A number of selected derivatives, spanning a range of 5 logP units, were characterized for their lipophilicity through RP-HPLC. A good linear correlation, with a slope close to 1.0, was observed between the experimentally determined RP-HPLC lipophilicity parameters (logk′w) and calculated logP (clogP) values, whereas a systematic difference in absolute values between the chromatographic parameters and in silico lipophilicity descriptors can be attributed mainly to silanophilic interactions between the H-bond acceptor SO2 group and free silanol groups on silica-based C18 columns, which results in increased retention times.
