128102-48-7

Upstream product

• 124-38-9 carbon dioxide 
• 14905-81-8 1-(isopropylthio)-4-methylbenzene 
• 106-53-6 para-bromobenzenethiol 
• 70398-89-9 1-bromo-4-(1-methylethylthio)benzene 

Relevant academic research and scientific papers

Metallation reactions. Part 35: A change of the regiochemistry in the metallation of (alkylthio)arenes

The metallation reaction of bromo(alkylthio)benzenes is described. The results show the complementarity of these reactions with the metal-hydrogen exchange reaction. In fact, monometallation of bromo(methylthio)benzenes afforded products substituted in para or meta or ortho to the thioethereal function while bimetallation led to αS,para, αS,meta and αS,ortho disubstituted products. Analogously, the monometallation of 4-bromo-(isopropylthio)benzene afforded para-monosubstituted and ortho,para-disubstituted products.

METALATION REACTIONS. XIV. REGIOSPECIFIC PREPARATION OF POLYSUBSTITUTED BENZENES VIA MONO- OR DI-LITHIATION REACTIONS OF AROMATIC THIOETHERS

The preparation of polyfunctionalized aromatic thioethers either by one-step dilithiation or by two successive one-flask monometalation reactions is described.By acting on 1 two equal or different electrophiles one on the thiomethyl group and one in the ortho-position with respect to it are introduced; by acting on 11 and on 35 the substitution involves the thiomethyl carbon atom and that in the ortho-position with respect to the alkoxy group.In the case of the homologeous isopropylthio (23) the substitution involves the two aryl carbon atoms in the ortho-position to both functions.In the case of the p-disubstituted isomers (49, 59) analogous behaviour to ortho isomers in one-step metalation reaction is observed, while the two hydrogen atoms in the ortho-positions to the methoxy group are substituted when two successive monometalations are employed.The metalation of 40 results low selective.The behaviour of 79 and 93 is analogous to 1, while 72, 88 and 96 undergo only one-step monometalation reactions.