Combining the Individual Reactions into Overall Transformations and Cycles

Olefin Slippage During Nucleophilic Addition to Alkenes 

The displacement places more positive charge on the carbon that is further from the metal. In other words, the displacement shifts the structure of the alkene complex toward the structure of an alkyl complex with a cat- 

Some experimental results support this notion. 

The crystal structure of the following complex reveals the Pd-C bond lengths shown. The bond lengths to carbons C and D are nearly identical, so this alkene has a symmetrical rj -structure. However, the bond lengths to carbons A and B are significantly different. Nucleophilic attack by alkoxide anions, enolates, and amines occurs at carbon A only, supporting the notion that slipping the alkene enhances its susceptibility to nucleophilic attack. 

Eisenstein, O., and Hoffmann, R. Activation of a Coordinate Olefin Toward Nucleophilic Attack. /. Am. Chem. Soc., 102,6148 (1980). 

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COMBINING THE INDIVIDUAL REACTIONS INTO OVERALL TRANSFORMATIONS AND CYCLES... 

Combining the Individual Reactions into Overall Transformations and Cycles... 

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