P-Tolylmagnesium bromide

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])...

A simple and efficient synthesis of juvabione (58) (c/. Vol. 1, p. 60 Vol. 5, p. 49 Vol. 4, p. 88), a sesquiterpenoid possessing juvenile hormone activity, has been achieved using a combination of hydroboration and carbonylation reactions cf. Scheme 6). A new efficient synthesis of ( )-a-curcumene (59) cf. Vol. 5, p. 51) involves reduction in situ (Li-NHs) of the alkoxide produced from p-tolylmagnesium bromide and 6-methylhept-5-en-2-one. ... 

Methylquinoxaline reacts with both alkyl and aryl magnesium compounds to give, after hydrolysis, 2-alkyl-, or 2-aryl-l,2-dihydro-3-methylquinoxalines. When the dihydro compound 2, derived from p-tolylmagnesium bromide, is heated in ethanol, isomerization occurs, and... 

Mt-Dunetfiylhenzyl Alcohol. at4-Dimethylben-zenemethanol p-tolylmethylcarbinol meihyl-p-tolylcarbi-nol 4 (o-hydroxyethyl)toluene 4-methyl-a-phenethyl alcohol l -p-tolyl-1-ethanol. CjH O m l wt 136.19. C 79.37%, H 8.88%, O 11,75%. Constituent of the essential oil from CurcumQ longa L., Ztngiberaceae and related plants Dieterie, Kaiser. Arch. Pharm. 271, 337 (1933). Prepd from p-tolylmagnesium bromide and acetaldehyde in ether v. 

A 1.2 M soln. of p-tolylmagnesium bromide in tetrahydrofuran added dropwise at room temp, to a stirred soln. of N-phenyl-N -tosyloxydiimide N-oxide in the same solvent, and stirred 2 hrs. at 50-60° 4 -methylazoxybenzene. Y 73%.— Similarly with n-butylmagnesium chloride phenylazoxybutane. Y 62%. F. e., also formation of sulfones, s. T. E. Stevens, J. Org. Ghem. 29, 311 (1964). 

Mesityl p-tolyl ketone and p-tolylmagnesium bromide gave a similar result. 

Stirred ethereal p-tolylmagnesium bromide Mg-pellets under Ng treated slowly at 0-5°... 

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