60973-46-8

Upstream product

• 6331-22-2 2-methyl-2-phenyl-[1,3]dithiane 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 603-76-9 1-methylindole 
• 96-54-8 N-Methylpyrrole 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 
• 5849-19-4 <1,3>dithian-2-yl-phenyl-methanol 
• 80637-22-5 (3-Chloro-propylsulfanylethynyl)-benzene 

Relevant academic research and scientific papers

Chiral Phosphoric Acid Catalyzed Enantioselective Ring Expansion Reaction of 1,3-Dithiane Derivatives: Case Study of the Nature of Ion-Pairing Interaction

Chiral counterion controlled asymmetric catalysis via an ion-pairing interaction has attracted immense attention in recent years. Despite a number of successful studies, the mechanistic elucidation of the stereocontrolling element in the ion-pairing interaction is rarely conducted and hence its nature is still far from being well understood. Herein we report an in-depth mechanistic case study of a newly developed enantioselective ring expansion reaction of 1,3-dithiane derivatives catalyzed by chiral phosphoric acid (CPA). An unprecedented enantioselective 1,2-sulfur rearrangement/stereospecific nucleophilic addition sequence was proven to be the stereoselective pathway. More importantly, by thorough investigation of the intrinsic nature of the stereospecific nucleophilic addition to the cationic thionium intermediate, we discovered that the key interaction in this process is the nonclassical C-H···O hydrogen bonds formed between the conjugate base of the CPA catalyst and the cationic intermediate. These C-H···O hydrogen bonds not only bind the catalyst to the substrates to form energetically favored states throughout the overall processes but also firmly maintain the relative positions of these fragments as the fixed contact ion pair to sustain the chiral information generated at the initial sulfur rearrangement step. This mechanistic case study provides a very clear understanding of the nature of the ion-pairing interaction in organocatalysis. The conclusion encourages the further development of the research field with the focus to design new organocatalysts and cultivate novel organocatalytic transformations.

Electronic control of product formation in the rearrangement of 1,3-dithian-2-yl-arylmethanols

1,3-Dithian-2-yl-phenylmethanols undergo efficient rearrangement to afford 2-phenyl-6,7-dihydro-5H-1,4-dithiepines. The reactions were found to show remarkable variation in products formation that is dictated by the substituents on the aryl ring.

New Applications of 2,4,6-Trichloro-1,3,5-triazine (TT) in Synthesis: Highly Efficient and Chemoselective Deprotection and Ring-Enlargement of Dithioacetals and Oxathioacetals

Efficient deprotection of a wide variety of 1,3-dithioacetals and 1,3-oxathiolanes to the corresponding carbonyl compounds at room temperature using a combination of 2,4,6-trichloro-1,3,5-triazine (TT) and dimethyl sulfoxide (DMSO) was investigated. In this way, 1,3-oxathioacetals and 1,3-dithioacetals of enolizable ketones were converted to the corresponding 1,4-oxathiepine and 1,4-dithiepine derivatives, respectively.

2,3-Dihydro-dithiin and -dithiepine-1,1,4,4-tetroxides: Small molecule non-peptide antagonists of the human galanin hGAL-1 receptor

The neuropeptide galanin modulates several physiological functions such as cognition, learning, feeding behavior, and depression, probably via the galanin 1 receptor (GAL-R1). Using an HTS assay based on 125I-human galanin binding to the human

Synthesis of six- and seven-membered heterocycles by reaction of 1-(2-chloroethylthio)-1-alkynes and 1-(3-chloropropylthio)-1-alkynes with alkali metal sulfide, selenide and telluride

Reaction of RCC-S-CH2CH2Cl (1, R=alkyl) compounds with dilithium disulfide (Li2S2) in ethanol gives 3-alkyl-5,6-dihydro-1,4-dithiins (2, n=2, X=S).With the alkali monosulfide, M2S, dehydrochlorination to (vinylthio)alkynes RCC-S-CH=CH2 (3) predominates.Interaction between 1, n=2, and M2Se or M2Te (M=Li or Na) in liquid ammonia gives rise to dehydrochlorination as well as to attack on chlorine with intermediate formation of alkynethiolates RCC-S- (4); if this reaction is carried out in ammonia-free ethanol, the desired 5,6-dihydro-1,4-thiaselenins and -thiatellurins (2, n=2, X=Se or Te) are, in some cases, obtained.The chloro sulfides RCC-S-(CH2)3Cl (1, R=alkyl or phenyl) with alkali metal sulfide, selenide and telluride yield respectively 3-alkyl- or 3-aryl-6,7-dihydro-5H-1,4-dithiepins, the corresponding 6,7-dihydro-5H-1,4-thiaselenepins and 6,7-dihydro-5H-thiatellurepins (2, n=3).When R in the starting compounds 2 is a Me3Si group, the unsubstituted compounds 2 (n=3, R=H) are formed.