The effect of anchoring substitution on the course of a cation olefin bicyclization. Crystal structure of (±)‐(2R, 3′R,5′S)‐2‐(3′‐tert‐Butyl‐5‐Isopropl‐5′‐Methyl‐1′‐Cyclopentenyl)‐1‐Cyclopentanone

Abstract

AbstractThe SnCl4−induced cyclization of aldehyde (Z)‐1 gives rise to a bicyclic alcohol in high yield, the rearranged structure of which was assigned via X‐ray diffraction of its oxidation product 2. The structure (C18H30O, P21/c, a = 11.253(1), b = 6.990(1), c = 22.260(4)Å, β = 78.17(2)°; Dm = 1.02(1) g. cm3, Dc (Z=4) = 1.017 g. cm−3) has been solved by direct methods and refined to a final R value of 0.086 for 1014 observed reflections.