title: Synthesis, cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine and its hydrochloride salt.
abstract: We report herein the synthesis and characterization of 9-(2-diallylaminoethyl) adenine. We evaluated two different synthetic routes starting with adenine where the optimal route was achieved through coupling of 9-(2-chloroethyl)adenine with diallylamine. The cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine hydrochloride salt resulted in low molecular weight oligomers in low yields. In contrast, 9-(2-diallylaminoethyl)adenine failed to cyclopolymerize, however, it formed a copolymer with SO₂ in relatively good yields. The molecular weights of the cyclopolymers were around 1,700-6,000 g/mol, as estimated by SEC. The cyclo-copolymer was stable up to 226 °C. To the best of our knowledge, this is the first example of a free-radical cyclo-copolymerization of a neutral alkyldiallylamine derivative with SO₂. These polymers represent a novel class of carbocyclic polynucleotides.
authors.affiliation: Department of Chemistry, American University of Beirut, Box 11-0236, Beirut, Lebanon. kb05@aub.edu.lb
authors.forename: Kamal H
authors.initials: KH
authors.lastname: Bouhadir
authors.forename: Lara
authors.initials: L
authors.lastname: Abramian
authors.forename: Alaa
authors.initials: A
authors.lastname: Ezzeddine
authors.forename: Karyn
authors.initials: K
authors.lastname: Usher
authors.forename: Nikolay
authors.initials: N
authors.lastname: Vladimirov
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D006868:Hydrolysis; D058105:Polymerization; D011119:Polynucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013458:Sulfur Dioxide / Q000737:chemistry; D013818:Thermogravimetry
chemical_list: C579372:9-(2-diallylaminoethyl)adenine; C579373:9-(2-diallylaminoethyl)adenine hydrochloride; D005609:Free Radicals; D011119:Polynucleotides; D012997:Solvents; D013458:Sulfur Dioxide; D000225:Adenine