High-Load, Oligomeric Dichlorotriazine: A Versatile ROMP-Derived Reagent and Scavenger

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• 作者：Alan Rolfe ; Donald A. Probst ; Kelly A. Volp ; Iman Omar ; Daniel L. Flynn ; Paul R. Hanson
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：November 21, 2008
• 年：2008
• 卷：73
• 期：22
• 页码：8785-8790
• 全文大小：282K
• 年卷期：v.73,no.22(November 21, 2008)
• ISSN：1520-6904

文摘

A new high-load, soluble oligomeric dichlorotriazine (ODCT) reagent derived from ring-opening metathesis polymerization (ROMP) is reported as an effective coupling reagent, scavenger of nucleophilic species, and activator of DMSO for the classic Swern oxidations. Two variants of this reagent ^2GODCT 4 and ^1GODCT 16, possessing theoretical loads of 5.3 and 7.3 mmol/g, respectively, have been synthesized. Preparation was accomplished via simple synthetic protocols affording free flowing powders, amenable for large-scale production. Removal of the spent oligomeric reagent was achieved via either precipitation of the spent reagent or simple filtration utilizing a silica SPE, followed by solvent removal, to deliver products in excellent yield and purity. In addition, the corresponding norbornenyl monomer 3 was successfully demonstrated in a couple-ROMP-filter protocol utilizing in situ polymerization, achieving comparable results versus the corresponding oligomeric variant.