Rotational propensities and identity of bond rupture in 1-cyano-2-methyl-3-(cis-propenyl) cyclopropanes.
Comparison of the rate of recemization with the rates of diastereomerization in the title compound allows the firm conclusion to be drawn that the theoretically weakest of the three cyclopropane bonds is preferentially broken irrespective of the multiplicity of the internal rotations involved. Incidentally, the effect of an adjacent chiral methyl group on internal rotational propensities is elucidated.
Department of Chemistry, Harvard University, Cambridge, Massachusetts 02138.
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von Eggers Doering
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Barsa