Polyaryl anion radicals via alkali metal reduction of arylurea oligomers

Frederick D. Lewis; Todd L. Kurth; Chris M. Hattan; Richard C. Reiter; Cheryl D. Stevenson

doi:10.1021/ol0496069

Polyaryl anion radicals via alkali metal reduction of arylurea oligomers

Frederick D. Lewis^*, Todd L. Kurth, Chris M. Hattan, Richard C. Reiter, Cheryl D. Stevenson

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

A series of N-methylated polyarylurea oligomers have been reduced with potassium metal in HMPA. These reductions result in the transient formation of arylurea anion radicals, which undergo reductive elimination of the urea linkages. The aryl moieties appear in the products as the anion radicals of oligoaryl systems. The reaction is intramolecular, and the sequencing in the polyaryl anion radical remains the same as in the polyarylureas due to the urea-enforced π-π stacking interactions.

Original language	English (US)
Pages (from-to)	1605-1608
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	10
DOIs	https://doi.org/10.1021/ol0496069
State	Published - May 13 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0496069

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abstract = "A series of N-methylated polyarylurea oligomers have been reduced with potassium metal in HMPA. These reductions result in the transient formation of arylurea anion radicals, which undergo reductive elimination of the urea linkages. The aryl moieties appear in the products as the anion radicals of oligoaryl systems. The reaction is intramolecular, and the sequencing in the polyaryl anion radical remains the same as in the polyarylureas due to the urea-enforced π-π stacking interactions.",

author = "Lewis, {Frederick D.} and Kurth, {Todd L.} and Hattan, {Chris M.} and Reiter, {Richard C.} and Stevenson, {Cheryl D.}",

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T1 - Polyaryl anion radicals via alkali metal reduction of arylurea oligomers

AU - Lewis, Frederick D.

AU - Kurth, Todd L.

AU - Hattan, Chris M.

AU - Reiter, Richard C.

AU - Stevenson, Cheryl D.

PY - 2004/5/13

Y1 - 2004/5/13

N2 - A series of N-methylated polyarylurea oligomers have been reduced with potassium metal in HMPA. These reductions result in the transient formation of arylurea anion radicals, which undergo reductive elimination of the urea linkages. The aryl moieties appear in the products as the anion radicals of oligoaryl systems. The reaction is intramolecular, and the sequencing in the polyaryl anion radical remains the same as in the polyarylureas due to the urea-enforced π-π stacking interactions.

AB - A series of N-methylated polyarylurea oligomers have been reduced with potassium metal in HMPA. These reductions result in the transient formation of arylurea anion radicals, which undergo reductive elimination of the urea linkages. The aryl moieties appear in the products as the anion radicals of oligoaryl systems. The reaction is intramolecular, and the sequencing in the polyaryl anion radical remains the same as in the polyarylureas due to the urea-enforced π-π stacking interactions.

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Polyaryl anion radicals via alkali metal reduction of arylurea oligomers

Abstract

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