84131-00-0

Upstream product

• 75507-25-4 2-(hydroxymethyl)-15-crown-5 
• 98-59-9 p-toluenesulfonyl chloride 
• 75507-17-4 benzyl 2,4,7,10,13-pentaoxacyclopentadecan-2-ylmethyl ether 

Downstream Products

• 121436-19-9 4-(1,4,7,10,13-Pentaoxa-cyclopentadec-2-ylmethoxy)-phenylamine 
• 87708-36-9 5-Decyl-2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-benzoic acid methyl ester 
• 95230-40-3 [5-Decyl-2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-phosphonic acid diethyl ester 
• 121436-17-7 3-(1,4,7,10,13-Pentaoxa-cyclopentadec-2-ylmethoxy)-phenylamine 
• 121436-20-2 4-Nitro-2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenylamine 
• 95206-51-2 [5-Decyl-2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-phosphonic acid monoethyl ester 
• 126128-21-0 [5-Decyl-2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-phosphonic acid 
• 121436-22-4 3,5-Dinitro-4-[2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenylamino]-benzonitrile 
• 121436-26-8 (2,4-Dinitro-6-trifluoromethyl-phenyl)-[4-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-amine 
• 121436-21-3 [2-(1,4,7,10,13-Pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-(2,4,6-trinitro-phenyl)-amine 
• 121436-23-5 (2,6-Dinitro-4-trifluoromethyl-phenyl)-[2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-amine 
• 121436-24-6 (2,4-Dinitro-6-trifluoromethyl-phenyl)-[3-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-amine 
• 121451-10-3 (2,4-Dinitro-6-trifluoromethyl-phenyl)-[2-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenyl]-amine 
• 121436-29-1 4-[2,4-Dinitro-6-(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethoxy)-phenylamino]-3,5-dinitro-benzonitrile 

Relevant academic research and scientific papers

SYNTHESES AND PROPERTIES OF ARENEDIAZONIUM AND ANILINIUM CATION LARIAT ETHER COMPLEXES: AN "OSTRICH MOLECULE" COMPLEX AND EVIDENCE FOR INTRAMOLECULAR SIDEARM - MACRORING INTERACTION

The preparation of several novel lariat ethers (macrocyclic crown polyethers having sidearms bearing pendant donor groups) is reported.These compounds are ethers derived from known 2-hydroxymethyl-15-crown-5 or -21-crown-7.The sidearms include 2-aminophenyl, 2,4-diaminophenyl, 2-nitrophenyl, 2-(3'-nitrobiphenyl), and 2-(3'-aminobiphenyl).In several cases, the amino groups were converted into ammonium salts which showed substantial stabilization by intramolecular hydrogen bonding.Likewise, an -NH2(1+)*BF3(1-) complex showed evidence of intramolecular hydrogen bonding.Diazotization of the aminobiphenyl residue produced an arenediazonium cation which underwent intramolecular crown complexation, as judged by infrared spectroscopic studies to form what we call an "ostrich molecule" complex.Addition of N,N-dimethylaniline to the intramolecular arenediazonium cation complex afforded an azo compound, but europium shift reagent studies showed clearly that the diazonium cation reacted outside the macroring.

Crown Cation Complex Effects. 20. Syntheses and Cation Binding Properties of Carbon-Pivot Lariat Ethers

In an effort devise synthetic cation binders that will mimic the behavior of naturally occuring ionophores such as valinomycin, we have prepared approximately 30 macrocyclic (crown) polyethers bearing flexible side chains attached to the macro ring at carbon.In many of these "carbon-pivot" compounds, the side chain contains one or more neutral donor groups that, if in a suitable geometrical arrangement, may provide additional solvation to the macro-ring-bound cation.Although such donors often enhanced the cation binding ability, overall, the increases in stability constants were modest.The physical resemblance and concept of "roping and tying" the cation suggest the name "lariat ethers".Syntheses of these molecules and binding by them of Na+ and K+ cations are reported and conclusions drawn about the structural requirements and cation binding efficacy of these materials.

Enhancement of Cation Binding in Lariat Ethers Bearing a Methyl Group at the Quaternary, Pivot Carbon Atom

A number of carbon-pivot lariat ethers have been prepared and compared, with their counterparts having a methyl group bonded to the side-arm-bearing or pivot carbon.All of the compounds examined are 15-crown-5 derivatives, and in this series, the methyl lariats invariably show a higher affinity for sodium than do the nonmethylated species.The results are less consistent in the case of potassium cation which is larger than the 15-crown-5 compound's cation binding hole.The enhanced stability constant observed for sodium with the methyl lariats is attributed to reduced s ide-arm mobility or conformational changes in either the side arm or macroring.

NOVEL LIPOPHILIC CROWN CARBOXYLIC ACIDS

Four novel ionizable crowns are formed from reactions of methyl 5-(n-decyl)salicylate with tosylates from hydroxymethyl-12-crown-4, -15-crown-5, -18-crown-6 and -21-crown-7 followed by hydrolysis.