Abstract
AbstractThis is a review of the pertinent literature on the subject of the stereochemistry of homolytic nonconcerted ring opening of small carbocycles. The data suggests that cyclopropane opens either without bond rotation or with a single rotation or with disrotatory double rotation; conrotatory double rotation has not yet been observed. Cyclobutane and cyclopentane undergo conrotatory ring opening that is coupled with another rotation to cause shearing of the bond to give a gauche 1,4‐ or 1, 5‐biradical. These biradicals apparently undergo bond formation with rearrangement via a least motion stereochemical pathway competitive with rotation around bonds to randomize the stereochemistry of the initially generated biradical.
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