Organic Chemistry

TS-Torquoselectivity from Global Conformational Profile



From global conformational profile and differential activation energies of conrotatory outward and inward ring openings of all the conformers, it is shown that (a) 3-OMe-cyclobutene must open exclusively outward, and (b) conformers exist for 3-CHO-, 3-COMe-, and 3-NO-cyclobutenes that will open outwards as well. All the conformers of 3-OMe-, 3-CHO-, 3-COMe-, and 3-NO-cyclobutenes are, respectively, within 5.6, 3.2, 4.0 and 2.6 kcal/mol and, hence, abundantly available at room temperature for reaction.

Version notes

We have included the results of conformational analysis of 3-introso-cyclobutene and its effect on torquoselectivity and, hence, made corresponding changes in the structures scheme (new structure 4 added) and also included Figure 4.


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