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A possible explanation for this difference in effect may come from Hammet studies we have carried out for competition reactions of substituted styrenes with various carbenoids (ref 9). In these studies, we found that vinyldiazoacetates and phenyldiazoacetates (jn contrast to simple diazoacetates) display considerable selectivity in competition studies with various styrenes and the reactivity correlates well with a σ+ scale rather than a σ scale. This would suggest that the benzylic carbon of the styrene has some carbocation character in the transition state of the cyclopropanation and is stabilized by resonance through to the aromatic substituent. Consequently, it is reasonable that the methoxy group would have a more significant effect on the diastereoselectivity of the 1,1-diarylethylene cyclopropanation than a nitro group. The influence of the nitro group would be primarily through a polar effect rather than a resonance effect and would be largely independent of aromatic ring orientation. For a general discussion, see: Hine, J. In Structural Effects on Equilibra in Organic Chemistry: John Wiley & Sons: New York, 1975; pp 55-105.
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