Oxime ether anions structure

Many of the same features of imine and imine anion structure previously discussed (Section 4.1.3.2) are apparent with hydrazones and their anions and with oxime ether anions. A number of investigations of the structure of A A -dialkylhydrazone and oxime ether anions as well as oxime dianions have been carried out. Most notable are the experimental studies of Collum and Clardy, " and the theoretical treatment by Glaser and Streitwieser. As might be expected, and as was observed for lithiated imine anions iyida supra), lithiated hydrazones exist in the solid as aggregates, with two lithiums coordinated to the aza anion system (Figure 3). ... 

The methylation of the oximes of (1-oxoaikyi)phosphonic diaikyl esters yields 0 or N derivatives depending on the structure of the arnbident anion the nature of the electrophile is also influential. Methyl iodide or dimethyl sulphate yields only methyl ethers. On the other hand diazomethane affords... 

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