M-dimethoxybenzene

As mentioned earlier, attempts to make medium-size rings by sulfurbridging reactions are fraught with difficulty, as linear polymers are often obtained. Reaction of m-dimethoxybenzene with disulfur dichloride in... 

At the same time, the 3-methoxycyclohexadienyl complex (Scheme 32) can also be prepared, presumably under kinetic conditions that do not allow isomerization of the double bonds. The key technique is acid-induced elimination of an alkoxy group, and the starting material is m-dimethoxybenzene. The addition of the malonate anion is at one of the two equivalent terminal positions, and from a direction anti to the iron. The product is a stable complex that may be purified by chromatography or may be decomposed oxidatively to free the organic ligand. 

The third compound studied is the 4-thio analog of mescaline, 4-methylthio-3,5-dimethoxyphenethylamine. This was prepared (see scheme II) by the reaction, of lithiated m-dimethoxybenzene with dimethyldisulfide to form 2,6-dimethoxythioanisole. This underwent bromination uniquely adjacent to the methoxy group, and the resulting bromodimethoxythioanisole underwent a smooth benzyne reaction with acetonitrile to form the benzyl cyanide shown, which was reduced to the desired end product (3) with aluminum hydride in THF. 

Acetyl- 3 - ethylpy razi ne 54 Butyl acetate 102 m-Dimethoxybenzene... 

Benzene, 1,3-dimethoxy- m-dimethoxybenzene 172a 174a, 174b, 603, 3370... 

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