63458-91-3

Upstream product

• 26923-87-5 2-acetoxyethyl-2'-tosyloxyethyl ether 
• 75-64-9 tert-butylamine 
• 119072-55-8 tert-butylisonitrile 
• 104-15-4 toluene-4-sulfonic acid 
• 754-10-9 2,2-dimethylpropionamide 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 118132-81-3 tert-Butyl-phosphorimidic acid triethyl ester 

Relevant academic research and scientific papers

Non-covalent bonded 1D-3D supramolecular salts from tert?butylamine and organic acids

Cocrystallization of the widely available simplest voluminous primary amine, tert?butylamine, with a set of acids got a total of 14 salts, which have been featured by XRD technique, Infrared spectra and elemental analysis. Their melting points were also surveyed. Their structural and supramolecular aspects are analyzed in detail. All compounds are ionic, with H-transferring to the NH2 of the tert?butylamine. The results unveil that among all the studied crystals the NH2 in L are protonated when the acids are deprotonated, the crystal packing is interpreted via the strong N–H?O H-bond from the NH3+ and the deprotonated acids. Apart from the N–H?O H-bond, the O–H···O H-bonds were also existed at 6 and 12. Salts 1 - 2 had the N–H?S H-bond. The N–H···Cl H-bond existed in 7. Further view of the crystal packing told that a different array of additional CH3···S, O···Cl, S···S, CH3···C, CH3···CH3, C–H···O/CH3···O, CH2···Cl, CH···N, CH3···π and π···π contacts help the stabilization and expansion of the whole structures. For the synergism of the various nonbonding contacts these structures had the hetero supramolecular synthons. Some classical synthons of R22(8), R42(8), R43(10) and R44(12), commonly present in solids of organic acids with amine, were again shown to be created in making these H-bonding nets.

Supported p-toluenesulfonic acid as a highly robust and eco-friendly isocyanide scavenger

We document here the use of polymer-supported p-toluenesulfonic acid as a highly effective, robust, economical and eco-friendly isocyanide scavenger. The herein described strategy circumvent the intense and repulsive odor of volatile isocyanides, enabling simplified and odorless workup and purifications. The usefulness of the new scavengers has been validated in a set of diverse isocyanide-based organic transformations and this approach is also amenable to parallel synthesis techniques.

SYNTHESIS OF STERICALLY HINDERED SECONDARY AMINOETHER ALCOHOLS

Severely sterically hindered secondary aminoether alcohols are prepared by reacting organic carboxylic, organic carboxylic acid halides, acid anhydrides or a ketene with an alkyl, alkaryl or alkylhalo sulfonate to yield a sulfonic. Carboxylic anhydride compound which is then reacted with a dioxane to cleave the ring of the dioxane, yielding a cleavage product which cleavage product is then aminated with an alkylamine and hydrolyzed with base to yield the severely sterically hindered secondary aminoether alcohol.

TRIETHYL PHOSPHITE IN ORGANIC SYNTHESIS. A FACILE, ONE-POT CONVERSION OF ALCOHOLS INTO AMINES

General protocols for converting primary, secondary, and tertiary alcohols into the corresponding primary amines are presented.

IMINOPHOSPHORANE-MEDIATED TRANSFORMATION OF TERTIARY ALCOHOLS INTO t-ALKYLAMINES AND THEIR N-PHOSPHORYLATED DERIVATIVES

Novel azidation of tertiary alcohols by means of trimetylsilyl azide in the presence of boron trifluoride etherate has been worked out.The Staudinger reaction of crude azides with triethyl phosphite affords the corresponding iminophosphoranes which can be directly transformed into diethyl N-(t-alkyl)phosphoroamidates or t-alkylamine tosylates.

Direct Conversion of Aliphatic Carboxamides to Alkylammonium Tosylates with benzene

The utility of benzene (2) as a "Hofmann reagent" has been explored.Treatment of various primary, aliphatic carboxamides (RCONH2, R = methyl, ethyl, isopropyl, tert-butyl, n-pentyl, n-heptyl, undecyl, allyl, benzyl, cyclobutyl, cyclohexyl) with 2 in acetonitrile at reflux gave the corresponding alkylammonium tosylates (RN+H3-OTs) in yields ranging from 57percent to 94percent.The alkylammonium tosylates separated directly from the solvent when the reaction mixtures were kept at room temperature or below.When α-phenylacetamide was allowed to react with 2 in ethanol, ethyl benzylcarbamate (4) was obtained in 50percent yield, a result consistent with the intermediate existence of benzyl isocyanate in this reaction.A mechanism for the conversion of carboxamides by 2 to alkylammonium tosylates, involving the initial formation of N-phenyl iodonio amides and their collapse to iodobenzene and alkyl isocyanates, is proposed.The reaction of malonamide with 2 in acetonitrile followed a divergent course: 2-(tosyloxy)malonamide (3) was obtained in ca. 81percent yield (crude).