94265-89-1

Upstream product

• 98-82-8 Isopropylbenzene 
• 97-39-2 1,3-Di(2-tolyl)guanidine 
• 41294-64-8 cumyl ethyl sulfide 
• 16325-88-5 α,α-dimethylbenzylmercaptan 
• 13125-70-7 (+-)-methyl-(1-phenyl-ethyl)-sulfide 
• 109-72-8 n-butyllithium 

Downstream Products

• 16325-88-5 α,α-dimethylbenzylmercaptan 
• 1428366-12-4 C₁₅H₂₇NOSSi 
• 1428365-94-9 (R_s)-2-phenylpropyl-2-sulfinamide 
• 1609168-59-3 C₁₅H₂₇NOSSi 
• 1428366-11-3 C₁₈H₂₂OS₂ 
• 1428366-61-3 C₁₉H₂₃NOS 
• 1428366-50-0 C₂₀H₂₅NOS 
• 1428366-48-6 C₂₁H₂₅NOS 
• 1428366-46-4 C₁₉H₂₉NOS 
• 1428366-45-3 C₁₇H₂₇NOS 

Relevant academic research and scientific papers

CHIRAL 2-ARYLPROPYL-2-SULFINAMIDE AND CHIRAL N-2-ARYLPROPYL-2-SULFINYLIMINES AND SYNTHESIS THEREOF

Provided herein are novel chiral sulfinamide and imine compounds. Also provided herein are methods of synthesizing novel chiral sulfinamide and imine compounds comprising simplified purification methods when compared to prior methods. The novel chiral sulfinamide and imine compounds are useful, for example, in the synthesis of complex natural products and pharmaceutical important compounds.

Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis

A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (Rs)-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.

Photosensitized electron transfer oxidation of sulfides: A steady-state study

The photosensitized electron-transfer oxidation of a series of ethyl sulfides RSEt (1, R = C12H25; 2, PhCH2CH 2; 3, PhCH2; 4, PhCMe2; 5, Ph2CH) has been examined in acetonitrile and the product distribution discussed on the basis of the mechanisms proposed. In nitrogen-flushed solutions, cleaved alcohols and alkenes are formed, whereas under oxygen, in reactions that are 10-70 times faster, sulfoxides and cleaved aldehydes and ketones are formed in addition to the afore-mentioned products. Two sensitizers are compared, 9,10-dicyanoanthracene (DCA) and 2,4,6-triphenylpyrylium tetrafluoroborate (TPP+BF4-), the former giving a higher proportion of the sulfoxide, the latter of cleaved carbonyls. The sulfoxidation is due to the contribution of the singlet oxygen path with DCA. Oxidative cleavage, on the other hand, occurs both with DCA and with TPP+ which is known to produce neither singlet oxygen nor the superoxide anion. This process involves deprotonation from the α position of the sulfide radical cation, but the TPP+ results suggest that O2.- is not necessarily involved and non-activated oxygen forms a weak adduct with the radical cation promoting α-hydrogen transfer, particularly with benzylic derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Reaction of singlet oxygen with some benzylic sulfides

Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C-S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.

METALATION REACTIONS. VII. METALATION OF BENZYLALKYL AND β-PHENETHYLALKYL SULFIDES

The products from the reaction between n-butyllithium and benzylalkyl and β-phenethylalkyl sulfides followed by carbonation, have been investigated by GLC/MS analysis.With benzylalkyl sulfides metalation occurs at the benzylic position, and the corresponding carboxylic acid can be isolated, but side products from Wittig like rearrangement, cleavage of the thioether bond, and aliphatic and aromatic substitution are also obtained.No benzylic metalation or Wittig-like rearrangement products are obtained from β-phenethyl sulfides: instead cleavage of the thioether bond and aliphatic and aromatic substitution occur.