✦ LIBER ✦

Simple and high yielding regioselective synthesis of 1,4,8-tri(carbamoylmethyl)-1,4,8,11-tetraazacyclo-tetradecane hydroiodide

✍ Scribed by István Lázár

Book ID: 104260373
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 108 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)02317-x

No coin nor oath required. For personal study only.

✦ Synopsis

Near quantitative synthesis of 1,4,8-tris(carbamoylmethyl)-l,4,8,11-tetraazacyclotetradecane hydroiodide (1) has been achieved by reacting the parent macrocycle 1,4,8,11-tetraazacyclotetradecane (cyclam) with iodoacetamide in acetone in the presence of diisopropylethylamine as a base. The reaction stops at the trisubstituted stage even in the presence of a large excess of the reactants. This process represents the first example of a solubility controlled regioselective synthesis of a polyazamacrocyclic complexing agent; the driving force is the exceptionally low solubility of 1 in the reaction medium. 1 was hydrolyzed in acidic medium to the corresponding acetate derivative 1,4,8-tris(carboxylmethyl)-1,4,8,11-tetraazacyclotetradecane (2) in high yield.

📜 SIMILAR VOLUMES

ChemInform Abstract: Simple and High-Yie

ChemInform Abstract: Simple and High-Yielding Regioselective Synthesis of 1,4,8-Tri(carbamoylmethyl)-1,4,8,11-tetraazacyclotetradecane Hydroiodide.

✍ Istvan Lazar 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 27 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Synthesis and physical properties of hig

Synthesis and physical properties of high-spin five-coordinate iron(II) complexes of 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane

✍ Hodges, Keith D.; Wollmann, Ronald G.; Barefield, E. Kent.; Hendrickson, David N 📂 Article 📅 1977 🏛 American Chemical Society 🌐 English ⚖ 827 KB

Synthesis, characterization and crystal

Synthesis, characterization and crystal structures of the boratranes: 2,10,11-trioxa-6-aza-1-boratricyclo[4.4.4.01,6] tetradecane (tri-n-propanolamine borate), and 3-(4-methoxy)phenoxymethyl-7,10-dimethyl-2,8,9-trioxa-5-aza-1-boratricyclo[3.3.3.01,5]-undecane

✍ Robert A. Franich; Brian K. Nicholson; Hank W. Kroese; Suzanne S. Gallagher; Rog 📂 Article 📅 2011 🏛 Elsevier Science 🌐 English ⚖ 430 KB

Synthesis of hexacyclo[5.4.1.02,6.03,10.

Synthesis of hexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecane-5,11-dione and its conversion to di-, tri-, and tetranitro-1,3-bishomopentaprismanes

✍ Paquette, Leo A. ;Nakamura, Koichi ;Engel, Peter 📂 Article 📅 1986 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 966 KB

Sulfenylation of the dianion of dimethyl tetracyclo[7.2.1 .O4~".Ob~'"]dodeca-2,7-diene-5,I2-dicarboxylate (9) with dimethyl disulfide delivered the exo,exo-bis(methylthi0) derivative 10a. Subsequcnt saponification and oxidative decarboxylation resultcd in transformation to tetracyclo[7.2.1 .04.''.06

Synthesis of 1-(3-tert-butyldimethylsilo

Synthesis of 1-(3-tert-butyldimethylsiloxy)phenyl-5,5-dimethyl-2,7,8-trioxabicyclo[4.2.0]octanes: new dioxetanes giving high chemiexcitation yields in thermolysis and in fluoride-induced CIEEL-decay

✍ Masakatsu Matsumoto; Junko Murayama; Masao Nishiyama; Yasuko Mizoguchi; Toshimit 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 105 KB

Dioxetanes with annelated six-membered ring, 1-(3-tert-butyldimethylsiloxy)phenyl-5,5-dimethyl-2,7,8-trioxabicyclo[4.2.0]octanes (2a-2c) were synthesized by singlet oxygenation of the corresponding aryl-substituted dihydropyrans (3). Thermolysis of 2a-2c gave the corresponding ketoesters (5a-5c) as