Studies in the oxidative ring-opening of catechols and o-benzoquinones. Lead tetraacetate versus the copper(I) chloride/pyridine/methanol system

Tetrahedron

Volumn 55, Issue 38, 1999, Pages 11519-11536

  Walsh, James G ^a   Furlong, Patrick J ^a   Byrne, Louise A ^b   Gilheany, Declan G ^a,b  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; CATECHOL DERIVATIVE; COPPER CHLORIDE; LEAD ACETATE; METHANOL; PYRIDINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033578812     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00651-1     Document Type: Article

References (48)

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2. 3. We use the cis,cis terminology to mean the general stereochemistry that places the carboalkoxy group and other alkene moiety on the same side of the double bonds. Individual compounds are of course named according to the E/Z nomenclature.
3. 4. Walsh, J. G.; Furlong, P. J.; Gilheany, D. G. manuscript in preparation.
4. 5. Specifically the intradiol dioxygenases such as pyrocatechase which are based on iron and models for which have been extensively investigated, for leading references see: Que, Jr., L.; Ho, R.Y.N. Chem. Rev. 1996, 96, 2607.
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6. 6. These are mostly but not exclusively metal assisted and as well as copper-and lead-based methods, include ruthenium: Matsumoto, M.; Kuroda, K. J. Amer. Chem. Soc. 1982, 104, 1433; rhodium: Bianchini, C.; Frediani, P.; Laschi, F.; Meli, A.; Vizza, F.; Zanello, P. Inorg. Chem. 1990, 29, 3402; vanadium: Russo, U.; Zareli, B.; Zanonato, P.; Vidali, M. Polyhedron 1991, 10, 1353; metal-assisted peracid/peroxide: Pandell, A. J.; Matras, W. E. J. Org. Chem. 1987, 52, 697.
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