Mechanistic alternatives in Lewis acid-catalyzed acyl halide-aldehyde cyclocondensations

Tetrahedron Letters

Volumn 40, Issue 36, 1999, Pages 6541-6543

  Nelson, Scott G ^a   Peelen, Timothy J ^a   Wan, Zhonghui ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID HALIDE; ALDEHYDE; ALUMINUM; KETENE DERIVATIVE;

ACID BASE BALANCE; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; ENZYME MECHANISM; POLYMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033520206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01309-X     Document Type: Article

References (7)

1. Nelson, S. G.; Wan, Z.; Peelen, T. J.; Spencer, K. L. Tetrahedron Lett. 1999, 40, 6535-6539.
2. Hyatt, J. A.; Raynolds, P. W. Org. Reacts. (Ny) 1994, 45, 159-646.
3. Brady has previously characterized acyl halide enolates formed under similar conditions and documented their divergent reactivity as both nucleophiles and as ketene precursors, see: (a) Brady, W. T.; Scherubel, G. A. J. Am. Chem. Soc. 1973, 95, 7447-7449.
4. Brady, W. T.; Scherubel, G. A. J. Org. Chem. 1974, 39, 3790-3791.
5. For a report of a dioxanone product derived from a related acyl halide-aldehyde condensation, see: Borrmann, D.; Wegler, R. Chem. Ber. 1966, 99, 1245-1251.
6. Dioxanone products emerge from typical enolate-aldol addition reactions under certain conditions, validating these reaction products as markers for enolate-derived aldol reactions, see: Wedler, C.; Ludwig, R.; Schick, H. Pure & Appl. Chem. 1997, 69, 605-608, and references cited therein.
7. Firl, J.; Runge, W. Angew. Chem., Int. Ed. Engl. 1973, 12, 668-669.