Cyclic alcohols of known configuration and conformation with bulky groups in either the 3-position, the 4-position, or in both positions have been added to an olefin by a free-radical reaction involving the 1-hydrogen of the alcohol. In every case, it was found that both the cis and trans configurations formed the same intermediate free radical and thus gave the same ratio of products, The products were formed by an approximate 66:34 ratio of equatorial to axial attack of olefin on a planar, intermediate free radical except in the coprostanols in which the ratio was reversed. It was found that a complete product separation and analysis could be done by thin layer chromatography. © 1964, American Chemical Society. All rights reserved.