Sulfone, methoxymethyl phenyl

This general procedure has also been extended to allow for the insertion of a methoxy-containing carbon. The uncat yzed addition of the lithium anion of methoxymethyl phenyl sulfone to ketones proceeds readily at low temperature in dimethoxyethane to form the intermediate adduct. Addition of a Lewis acid (ethylaluminum dichloride or diisobutylaluminum diisopropylamide) directly to the reaction mixture effects the rearrangement reaction to pr uce the ring-expanded a-methoxy ketone. This sequence, illustrated by the example in Scheme 28, is limited to the expansion of four- and five-membered ring ketones. ... 

In a similar vein, the adducts derived from the anion of methoxymethyl phenyl sulfone and cyclic ketones rearrange on Lewis acid catalysis (Scheme 13). This rearrangement is quite stereospecific, in that a single diastereoisomer is formed and it is the most substituted group which migrates. Similar results were obtained with adducts derived from phenyl thiomethyl phenyl sulfone (Scheme 14). ... 

The Rf value of three degradates, 2 6 -diethlanaline, 2-chloro-2 6 -diethlacetanilide, and ethane sulfonic acid [2-[(2,6-dietfayl-phenyl) (methoxymethyl) amino]-2-oxoethanesulfonic acid, were similar with an Rf value of 0.65. The oxoac tic acid metabolite (OAA) [(2,6-diethylphenyl) (methoxymethyl) amino] oxoacetic acid had an Rf value of 0.45 (Figure 2). Other bands of more polar, unidentified C compounds were found in some treatments and had Rf values ranging from 0.05 to 0.35. 

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