18979-80-1

Upstream product

• 156-43-4 4-Ethoxyaniline 
• 54337-43-8 1-oxaspiro[2.5]octa-4,7-dien-6-one 
• 107-03-9 1-thiopropane 
• 637-88-7 1,4-Cyclohexanedione 
• 123-30-8 4-amino-phenol 
• 696-63-9 4-Methoxybenzenethiol 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 62291-63-8 p-methoxyphenyl propyl sulfide 

Downstream Products

• 36089-70-0 C₁₅H₁₅NO₃S 
• 36089-95-9 C₁₅H₁₅NO₅S 
• 36089-83-5 C₁₅H₁₅NO₄S 
• 163277-34-7 4-Propylsulfanyl-benzene-1,2-diol 
• 163277-37-0 4-Propylsulfanyl-[1,2]benzoquinone 

Relevant academic research and scientific papers

Site-Selective Synthesis of Aryl Sulfides via Oxidative Aromatization of Cyclohexanones with Thiophenols

We have introduced a metal-free facile access for the thiolation/aromatization of cyclohexanones with thiophenols to the corresponding aryl sulfides. The dehydroaromatic reaction of non-aromatic cyclohexanones proceeded smoothly using oxygen as a green oxidant.

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram-scale operations, and readily applied for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

A concise synthesis of thyroxine (T4) and 3,5,3'-Triiodo-L-thyronine (T3)

The mono- and di-iodo derivatives of 1-oxaspiro[2,5]bicycloocta-4,7-dien-6-one, 8 and 9, reacted readily with 3,5-diiodo-L-tyrosine at pH 8.0 to give 3,5,3'-triiodo-L-thyronine (T3) and thyroxine in 70% and 94% yields respectively. In turn, 8 and 9 were prepared by the sodium bismuthate oxidation of their corresponding iodinated p-hydroxybenzyl alcohol derivatives, 6 and 7 in 32% and 37% yields.