4-Tolylmagnesium bromide

Ethyl 2,4-diphenylbutanoate, 47, 72 Ethyl 2,3-diphenylpropionate, 47, 74 Ethyl isocyanide, 46, 76, 77 Ethylmagnesium bromide, use with ferric chloride in cyclization of di-chloroacetone -tolylmagnesium bromide adduct to l-/>-tolylcy-clopropanol, 47,108 Ethyl nit ropheny lace late, reaction... 

In contrast to the widely investigated stereochemistry of nucleophilic substitution at optically active tricoordinate sulfur, there have been few similar studies with optically active tetracoordinate sulfur systems. Sabol and Andersen (174) were the first to show that the reaction of p-tolylmagnesium bromide with (-)-menthyl phenyl-methane[ 0- 0]sulfonate 140 proceeds with inversion of configuration. Thus, the Grignard reaction at the sulfinyl and sulfonyl centers takes place with the same stereochemistry. 

Table 1-7. Catalyst effect on the Grignard (p-tolylmagnesium bromide) coupling with 2-(methylthio)-4,4-dimethyl-2-oxazoline (data from [112])...

In 1964, thanks to the development of modern techniques, especially electron-spin resonance (ESR), a direct proof could be given of the occurrence of radicals in the reaction of Grignard reagents, such as ethylmagnesium iodide, phenylmagnesium bromide, and /Jflra-tolylmagnesium bromide, in tetrahydrofuran (THF) with aromatic ketones, such as 4-chlorobenzophenone, 4-aminobenzophenone, 4-methoxybenzophenone, 4,4 -dimethoxybenzophenone, acetophenone, and 4-bromoacetophenone [34]. 

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