Hypersensitive radical probe studies of Gif oxidations

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 819-822

  Newcomb, Martin ^a   Simakov, Pavel A ^a   Park, Seung Un ^a,b  

^a WAYNE STATE UNIVERSITY   (United States)

^b Konkuk University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; RADICAL;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS;

EID: 0030043907     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02330-5     Document Type: Article

References (25)

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11. Gif oxidation of 3-carene, a potential mechanistic probe substrate, has been reported; see Lee, K.-W.; Kim, S.-B.; Kim, S.-B.; Barton, D. H. R.; Doller, D. Bull. Korean Chem. Soc. 1991, 12, 459-460.
12. 2 produced all three cresl isomers in addition to benzyl alcohol and benzaldehyde, whereas oxidations with t-BuOOH gave no cresols. An authentic sample of the p-phenol formed from probe 1H was available for GC-mass spectral identification. The structures of the o- and m-phenols from 1H were deduced from their mass spectra (essentially identical to that of the p-phenol) and GC retention times. On the basis of the observed behavior in GC analysis of cresol isomers on a Carbowax column, the o-phenol eluted with a considerably shorter retention time than the other two. The structures of phenolic products from probe 1M were deduced from their mass spectral fragmentation patterns. For probe 1P, phenolic products were obtained as deduced by mass spectrometry, but no attempt was made to assign the structures.
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