14613-34-4

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 90073-34-0 (Benzylimido)phosphorsaeure-triaethylester 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 103-81-1 Benzeneacetamide 
• 80-48-8 methyl p-toluene sulfonate 
• 100-46-9 benzylamine 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 85231-92-1 diethyl N-tert-butoxycarbonyl-N-phenylmethylphosphoramidate 
• 351-70-2 benzyl trifluoroacetate 
• 100-51-6 benzyl alcohol 
• 88333-03-3 Benzyl isocyanide 
• 622-79-7 benzyl azide 
• 100-39-0 benzyl bromide 
• 6165-76-0 propargyl p-toluenesulfonate 

Downstream Products

• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Crystal structures of seven molecular salts derived from benzylamine and organic acidic components

Cocrystallization of the commonly available organic amine, benzylamine, with a series of organic acids gave a total of seven molecular salts with the compositions: (benzylamine): (p-toluenesulfonic acid) (1) [(HL)+ · (tsa?)], (benzylamine): (o-nitrobenzoic acid) (2) [(HL+) · (onba)?], (benzylamine): (3,4-methylenedioxybenzoic acid) (3) [(HL+) · (mdba?)], (benzylamine): (mandelic acid) (4) [(HL+) · (mda?)], (benzylamine): (5-bromosalicylic acid)2 (5) [(HL+) · (bsac?) · (Hbsac)], (benzylamine): (m-phthalic acid) (6) [(HL+) · (Hmpta?)], and (benzylamine)2: (trimesic acid) (7) [(HL+)2 · (Htma2?)]. The seven salts have been characterised by X-ray diffraction technique, IR, and elemental analysis, and the melting points of all the salts were also reported. And their structural and supramolecular aspects are fully analyzed. The result reveals that among the seven investigated crystals the NH2 groups in the benzylamine moieties are protonated when the organic acids are deprotonated, and the crystal packing is interpreted in terms of the strong charge-assisted N[sbnd]H?O hydrogen bond formation between the ammonium and the deprotonated acidic groups. Except the N[sbnd]H?O hydrogen bond, the O[sbnd]H?O hydrogen bonds (charge assisted or neutral) were also found at the salts 4–7. Further analysis of the crystal packing of the salts indicated that a different family of additional CH[sbnd]O/CH2[sbnd]O, CH[sbnd]π/CH2[sbnd]π, O[sbnd]O, and O[sbnd]Cπ associations contribute to the stabilization and expansion of the total high-dimensional (2D-3D) framework structures. For the coexistence of the various weak nonbonding interactions these structures adopted homo or hetero supramolecular synthons or both. Some classical supramolecular synthons, such as R42(8), R43(10) and R44(12), usually observed in organic solids of organic acids with amine, were again shown to be involved in constructing most of these hydrogen bonding networks.

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.

One-Pot synthesis of sulfonamides from primary and secondary amine derived sulfonate salts using cyanuric chloride

A convenient, mild and efficient one-pot synthesis of new sulfonamides is described. The reaction of primary or secondary amine derived sulfonate salts in the presence of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as solvent at room temperature gives the corresponding sulfonamides in good to excellent yields. Georg Thieme Verlag Stuttgart.

Synthesis of alkylammonium tosylates with poly{[4-hydroxy(tosyloxy)iodo] styrene}

Several primary carboxamides (RCONH2) were converted to the corresponding alkylammonium tosylates (RN+H3 -OTs) with poly{[4-hydroxy (tosyloxy) iodo]styrene} (PSHTIB) in yields ranging from 60% to 90%.

Preparation and reactivity of 1,3,5,7-tetrakis[4-(diacetoxyiodo)phenyl] adamantane, a recyclable hypervalent iodine(III) reagent

A wide range of oxidative reactions are mediated by novel, nonpolymeric, and recyclable hypervalent IIII reagents (e.g. 2). In all cases, tetraiodide 1 was recovered nearly quantitatively in pure form after a simple workup. Reoxidation of 1 to

New protocol for converting alcohols into amines

The reactions between diethyl N-(t-butoxycarbonyl)phosphoramidate 1, diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP) and primary or secondary alcohols lead to the corresponding diethyl N-alkyl-N-(t-butoxycarbonyl)phosphoramidates 2a-o. Deprotection of crude 2 by refluxing with p-toluenesulfonic acid monohydrate in ethanol affords ammonium tosylates 3a-o in moderate to good overall yields. The N-alkylation of 1 proceeds stereoselectively with complete inversion of the configuration of the alkyl group.

An optimized version of Gabriel-type nucleophilic amination

N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t- butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-I. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol-affords ammonium tosylates 3a-I in reasonable yields.

KINETICS AND MECHANISM OF AMINOLYSIS OF PROPARGYL AND 1-METHYL-PROPARGYL ARENESULPHONATES

Kinetic studies were carried out on the aminolysis of propargyl and 1-methylpropargyl arenesulphonates in acetonitrile at 45.0 deg C.The cross-interaction constants, ρxz and βxz, are similar to, but smaller than, those for the SN2 processes at other primary and secondary carbon centers.Compared with the allyl series, the smaller magnitude of ρxz and βxz reflects a looser transition state, which in turn leads to a lower rate despite the greater Taft's ?* value and the lower intrinsic (ΔE0) and thermodynamic barriers (ΔE0).

Bimolecular Nucleophilic Substitution (SN2) Reactions of Neopentyl Arenesulfonates with Anilines and Benzylamines in Methanol

Bimolecular nucleophilic substitution (SN2) reactions of neopentyl arenesulfonates with anilines and benzylamines in methanol at 55.0 deg C are reported.The tightness of the transition state (TS) is similar to that for other typical SN2 processes at a primary alkyl carbon centre based on the magnitude of the cross-interaction constant ρxz (0.30) between the substituents in the nucleophile (X) and leaving group (Z).The TS variation is in accord with that predicted by the potential energy surface diagram, which in turn is consistent with the positive sign of ρxz; a later TS is obtained with a weaker nucleophile and nucleofuge.Taft's polar substituent constant, ?*, for the trimethylsilyl group is estimated to be -0.48 by using a factor of 1.875 for the fall-off of ?* from the tert-butyl to the neopentyl group and extrapolating from the experimental Taft plot.

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.