19117-30-7

Upstream product

• 931-59-9 benzenesulfenyl chloride 
• 108-98-5 thiophenol 
• 108-18-9 diisopropylamine 
• 805232-85-3 2-benzyloxymethyl-2,5-dimethyl-furan-3-one 
• 66168-29-4 N-methyl-N,S-diphenylthiohydroxylamine 
• 34690-49-8 N,N-(Diphenyl)benzenesulfenamide 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 66633-64-5 benzenesulfinic acid diisopropylamide 
• 64826-51-3 phenyl 1-oxo-pyridin-2-yl disulfide 
• 113435-66-8 (Ν,Ν-diisopropylamino)tricyclo[3.3.1.1^3,7]dec-1-ylmethanone 
• 20308-62-7 N,N-diisopropyl-3-phenylpropionamide 
• 61259-25-4 N,N-diisopropylcyclohexanecarboxamide 

Relevant academic research and scientific papers

Copper-catalyzed synthesis of sulfenamides utilizing diaryl disulfides with alkyl amines

The copper-catalyzed coupling of diaryl disulfides with alkyl amines can afford various sulfenamides in good yields. Furthermore, the present reaction is efficient and can be used for both of the aryl sulfide groups on disulfide. Georg Thieme Verlag Stutt

A palladium-catalyzed regio- and stereoselective four-component coupling reaction

(Chemical Equation Presented) Pd(PPh3)4 catalytically assembles sulfenamide, alkyne, carbon monoxide, and diphenyl diselenide regio- and stereoselectively in a one-pot four-component coupling reaction to yield (Z)-β-selenyl acrylamid

Further enolate alkylation studies of 2,5-dimethyl-3(2H)-furanone

Heterocyclic ketones, such as 2,5-dimethyl-3(2H)-furanone, provide multifunctional intermediates to various compounds. One property of these that has proven useful is the ability to alkylate the γ′-position of the dienolate. This report demonstrates the versatility of γ′-dienolate substitutions as employed toward syntheses of certain natural products and highly reactive electrophiles provide the best substrates for efficient substitution.

LDA-promoted decomposition of benzenesulfenamides. A route to aminyl radicals by dioxygen oxidation of lithium amides

The LDA-promoted decomposition of N-monosubstituted sulfenamides 1a-d occurs through the formation of thioaminyl anions, which undergo oxidation either at sulfur, with formation of sulfonamides, or at nitrogen, with formation of thioaminyl radicals, depending on the nature of the 4'-substituent. The reaction of N,N-disubstituted sulfenamides 1e-h proceeds through the intermediacy of a lithium complex capable of generating aminyl radicals via sulfenyl group transfer to the di-iso-propylamido anion and subsequent aerial oxidation of the resulting lithium amides 3e-h.

N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides

The reaction between an acyl derivative of N-hydroxypyridine-2(1H)- thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both synthetic and biological value. In sterically demanding cases, Barton PTOC esters were more reactive towards benzenesulfenamides than to the corresponding free amines.