Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 22, Pages 8785-8790Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801578f
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Funding
- NCRR NIH HHS [P20 RR015563, P20 RR015563-06] Funding Source: Medline
- NIGMS NIH HHS [R41 GM076765, P50 GM069663, P50 GM069663-05, R41 GM076765-01] Funding Source: Medline
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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 (ODCT)-O-2G 4 and (ODCT)-O-1G 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.
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