48147-55-3

Upstream product

• 50-00-0 formaldehyd 
• 36744-90-8 S,S-Diphenylsulfilimine 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 88070-48-8 N-methylbenzamide 
• 32133-82-7 Martins sulfurane 
• 74-89-5 methylamine 

Relevant academic research and scientific papers

Synthesis of phosphorus- and sulfur-stabilized carbone (Me)Ph2P→C←SPh2(= NMe)

Iminosulfane(phosphane)carbon(0) (iSPC) [(Me)Ph2P→C←SPh2(= NMe): 1] is generated by the deprotonation of corresponding cationic salt 1·H, which is obtained from the reaction of iminosulfonium methylide with Ph2PCl and subsequent P-methylation. Density functional theory calculations reveal that the electronic structure of 1 has two lone pairs of electrons at the carbon center. First and second proton affinity values are theoretically calculated to be 287.2 and 187.0 kcal mol-1, respectively. The highest occupied molecular orbital (HOMO) energy level of 1 is higher energy than that of bis(iminosulfane)carbon(0) (BiSC: [(MeN =)Ph2S→C←SPh2(= NMe)]). The reactivities of these lone pairs of electrons are demonstrated by the C-diaurated complex.

Preparation of N-alkyl-S,S-diphenylsulfimides by the reaction of N-unsubstituted S,S-diphenylsulfimide with borane-pyridine

The reaction of an N-unsubstituted S,S-diphenylsulfimide1 with aldehydes or ketones in the presence of a borane-pyridine complex and acetic acid in benzene at 40°C affords the corresponding N-alkyl-S,S- diphenylsulfimides. Since this reaction does not form the N,N-dialkylated aminosulfonium salt, this method provides a convenient preparation of N-monoalkylsulfimides without the necessity for a difficult separation of the products by column chromatography due to their similar Rf values. The mechanism of formation is discussed. Georg Thieme Verlag Stuttgart.

Synthesis, structure, and reactivity of iminosulfonium ylides bearing an α-carbonyl group

Treatment of methyl(methylimino)diphenylsulfonium tetraphenylborate (3) with NaH and subsequent acylation produced a new type of iminosulfonium ylides bearing an α-carbonyl group 5. The molecular structure of iminosulfonium phenacylide 5a was determined by X-ray crystallographic analysis. The ylide 5 reacted further with methyl triflate affording the corresponding novel alkylidenesulfonium salts 6.