Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 4, Pages 1665-1669Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo302592g
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Funding
- American Chemical Society Petroleum Research Fund
- Arnold and Mabel Beckman Foundation Scholars Program
- Towsley Foundation
- NSF [CHE-1148719, CHE-0922623]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1148719] Funding Source: National Science Foundation
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An analysis of the palladium-catalyzed activation of carbon-carbon single bonds within triarylmethanols has led to a greater understanding of factors influencing the beta-aryl elimination process responsible for C-C bond cleavage. A series of competition reactions were utilized to determine that beta-aryl elimination of aryl substituents containing ortho-substitution proceeds with significant preference to unsubstituted phenyl rings. Further experiments indicate that substrates containing either strongly donating or withdrawing substituents are cleaved from triarylmethanols more readily than relatively neutral species.
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