Conformational dynamics of three substituted decahydronaphthalenes

Abstract

The thermodynamic parameters for equilibrium of the chair-chair conformational enantiomorphs of 8a-methyl-cis-decahydronaphthalen-4a-yl acetate, E_a 67.1 ± 3 kJ mol^-1, ΔH^‡ 64.5 ± 3 kJ mol^-1,4a-chloro-8a-methyl-cis-decahydronaphthalene, E_a 73.6 ± 2.5 kJ mol^-1, ΔH^‡ 70.8 ± 2.5 kJ mol^-1 and the chair-chair conformers of (1α,4aα,8aα)-4a-methyldecahydronaphthalene-1,8a-diyl diacetate:conformer (A) to (B) E_a 68.9 ± 4 kJ mol^-1, ΔH^‡ 66.7 ± 4 kJ mol^-1, and conformer (B) to (A) E_a 66.8 ± 4 kJ mol^-1, ΔH^‡ 64.5 ± 4 kJ mol^-1 have been determined from ¹³C n.m.r. studies.