高负载寡聚单胺盐酸盐：通过自由基开环聚合轻松制备及其作为亲电试剂清除剂的应用。
High-load, oligomeric monoamine hydrochloride: Facile generation via ROM polymerization and application as an electrophile scavenger.
作者信息
Stoianova Diana S, Yao Lei, Rolfe Alan, Samarakoon Thiwanka, Hanson Paul R
机构信息
Materia Inc., 60 N. San Gabriel Blvd., Pasadena, CA 91107.
出版信息
Tetrahedron Lett. 2008;49(29-30):4553-4555. doi: 10.1016/j.tetlet.2008.05.011.
Abstract
A new high-load, oligomeric monoamine hydrochloride (OMAm*HCl) derived from ring-opening metathesis polymerization (ROMP) of norbornene methylamine is reported. This oligomeric amine has been shown to be an effective scavenger of acid chlorides, sulfonyl chlorides and isocyanates. The reagent can be synthesized in a straightforward protocol from the Diels-Alder reaction of dicyclopentadiene (DCPD) 1 with allylamine (neat), formation of the corresponding ammonium salt and subsequent ROM polymerization to afford the desired oligomeric ammonium salts.
摘要
据报道，一种由降冰片烯甲胺的开环易位聚合（ROMP）衍生而来的新型高负载低聚物单胺盐酸盐（OMAm*HCl）。这种低聚物胺已被证明是一种有效的酰氯、磺酰氯和异氰酸酯清除剂。该试剂可通过双环戊二烯（DCPD）1与烯丙胺（纯品）的狄尔斯-阿尔德反应、相应铵盐的形成以及随后的ROMP聚合，以一种直接的方法合成，从而得到所需的低聚铵盐。
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J Comb Chem. 2008 Mar-Apr;10(2):195-203. doi: 10.1021/cc7000869. Epub 2007 Dec 29.
2
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J Org Chem. 2007 Apr 27;72(9):3194-8. doi: 10.1021/jo0620260. Epub 2007 Apr 4.
3
One-step synthesis of oxazoline and dihydrooxazine libraries.
J Comb Chem. 2007 May-Jun;9(3):473-6. doi: 10.1021/cc060159t. Epub 2007 Mar 29.
4
Solid-phase synthesis of polymers using the ring-opening metathesis polymerization.
J Am Chem Soc. 2005 Oct 26;127(42):14536-7. doi: 10.1021/ja053931p.
5
Solution-phase parallel synthesis of a 1,2,7-trialkyl-1H-imidazo[4,5-g]quinoxalin-6-ol library scaffold.
J Comb Chem. 2005 Sep-Oct;7(5):657-64. doi: 10.1021/cc050005y.
6
High-load, ROMP-generated oligomeric bis-acid chlorides: design of soluble and insoluble nucleophile scavengers.
Org Lett. 2003 Nov 13;5(23):4241-4. doi: 10.1021/ol0352759.
7
ROMP-generated oligomeric sulfonyl chlorides as versatile soluble scavenging agents.
Org Lett. 2003 Jan 23;5(2):105-7. doi: 10.1021/ol0270273.
8
Dendrimers as support for recoverable catalysts and reagents.
Chem Rev. 2002 Oct;102(10):3717-56. doi: 10.1021/cr0103874.
9
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Chem Rev. 2002 Oct;102(10):3693-716. doi: 10.1021/cr0103524.
10
Using soluble polymers to recover catalysts and ligands.
Chem Rev. 2002 Oct;102(10):3345-84. doi: 10.1021/cr010343v.
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