115412-23-2

Upstream product

• 104-93-8 p-methylanizole 
• 111-88-6 Octanethiol 
• 104-82-5 4-Methylbenzyl chloride 
• 115412-19-6 Thioacetimidic acid octyl ester; hydrobromide 
• 111-83-1 1-bromo-octane 

Downstream Products

• 822-27-5 dioctyl disulfide 
• 111-88-6 Octanethiol 
• 106-42-3 para-xylene 
• 538-39-6 1,2-di-p-tolylethane 
• 4498-99-1 4-methylbenzylthiol 
• 87630-23-7 1-p-tolyl-nonane 

Relevant academic research and scientific papers

Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides

A new reductive preparation of unsymmetrical sulfides from esters and thiols in the presence of InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 as the reductant was developed. This protocol was applied to not only benzoic acid esters that have a methoxy, methyl, chloro, bromo, iodo, or trifluoromethyl group on the aromatic ring but also aliphatic acid esters with either aromatic or aliphatic thiols. A reaction mechanism is proposed by using Hammett plot results and several control experiments. The reductive preparation of unsymmetrical sulfides from esters and thiols by using InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 was developed. Several mechanistic studies support that the present transformation proceeds through O,S-and S,S-acetals as the reaction intermediates. TMDS = 1,1,3,3-tetramethyldisiloxane, R = aliphatic group.

Mechanism of the Solution-Phase Reaction of Alkyl Sulfides Atomic Hydrogen. Reduction via a 9-S-3 Radical Intermediate

The low selectivity of benzyl alkyl sulfide fragmentation subsequent to its reaction with atomic hydrogen is indicative of a reaction that proceeds via an early transition state. The competitive reduction of a series of substituted-benzyl alkyl sulfides was insensitive to the substituent on the aromatic ring (ρ = -0.13, r = 0.99). The relative rates of fragmentation of a series of the substituted-benzyl alkyl sulfides gave a V-shaped Hammett plot. Both electron-donating and electron-withdrawing groups destabilized the transition state (ρ = +0.99, r = 0.999; ρ = -0.82, r = 0.992). Since the relative rates of disappearance of the alkyl benzyl sulfides are not substituent dependent, but the relative rates of fragmentation are, a 9-S-3 intermediate is preferred as the structure leading to products.

An Efficient Synthesis of Unsymmetrical Sulfides Using Liquid-Liquid Phase-Transfer Catalysis

The reaction between alkyl ethaneimidothioate hydrohalides (1-alkylthioethaniminium halides) and organic halides gives unsymmetrical sulfides in good yields under liquid-liquid phase-transfer conditions.