Conformation of isobutyl, 2,2-dibromoethyl, and 2-methoxypropyl side chains on cyclohexane and tetrahydropyran ring systems

Article abstract of DOI:10.1002/1099-0690(200105)2001:10<1857::AID-EJOC1857>3.0.CO;2-4

An isobutyl group placed equatorially in the 2-position of a 1-equatorially substituted cyclohexane adopts a preferred conformation (cf. 5). This also holds when it is placed in the 2-position on a 3-equatorially substituted tetrahydropyran (cf. 6). The same conformational preference is found for 2-methoxypropyl residues in the 2-position of 3-substituted tetrahydropyrans (cf. 8 and 10). The latter compounds chelate lithium cations as analogues of 1,2-dimethoxyethane. Through this complexation, it is possible to effect a change in the side chain conformation.