High-load, Oligomeric Dichlorotriazine: a Versatile ROMP-derived Reagent and Scavenger

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2008 Oct 22

PMID 18937412

Citations 13

Authors

Alan Rolfe

Donald A Probst

Kelly A Volp

Iman Omar

Daniel L Flynn

Paul R Hanson

Affiliations

Soon will be listed here.

Abstract

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 (2G)ODCT 4 and (1G)ODCT 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.

Citing Articles

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