Bleach/Acetic Acid-Promoted Chlorinative Ring Expansion of [2.2.1]- and [2.2.2]-Bicycles

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3899-3902

  Ruggles, Erik L ^a   Maleczka Jr , Robert E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CHLORINE; FUSED HETEROCYCLIC RINGS; HYPOCHLORITE SODIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ACETIC ACID; BICYCLO COMPOUNDS, HETEROCYCLIC; CHLORINE; MOLECULAR STRUCTURE; SODIUM HYPOCHLORITE;

EID: 0038680322     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0267331     Document Type: Article

References (26)

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2. (b) see also Johnson, C. R.; Cheer, C. J.; Goldsmith, D. J. J. Org. Chem. 1964, 29, 3320-3323.
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6. Johnson and Herr (ref 1a) reported GC yields.
7. Johnson's GLC analysis indicted four major and two unidentified minor peaks. It is likely that one of these unidentified products was 6.
8. 2Cl protons making two conformers possible. Johnson used aromatic solvent-induced shifts of 3 to deduce the preferred conformer shown below. NOE data are consistent with this model. (For aromatic solvent-induced shifts, see: Bhacca, N. S.; Williams, D. H. In Applications of NMR Spectroscopy in Organic Chemistry; Holden-Day: San Francisco, 1964; Chapter 7.) (Matrix Presented)
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10. (b) This work was carried out with "regular" Clorox, which is ∼0.75 M in NaOCl. This product is being replaced by "ultra" Clorox, which is more alkaline and concentrated (∼0.83 M).
11. 2/1 g of compound) with EtOAc/hexane as the eluent. See Supporting Information for additional details.
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25. For examples of β-chloroketones in organic synthesis, see: (a) Zoretic, P. A.; Bendiksen, B.; Branchaud, B. J. Org. Chem. 1976, 41, 3767. (b) Krause, H.-J. DE Patent 29 25 521, 1981. (c) Miller, J. A.; Ullah, G. M.; Welsh, G. M.; Mallon, P. Tetrahedron Lett. 2001, 42, 2729-2731.
26. For examples of β-chloroketones in organic synthesis, see: (a) Zoretic, P. A.; Bendiksen, B.; Branchaud, B. J. Org. Chem. 1976, 41, 3767. (b) Krause, H.-J. DE Patent 29 25 521, 1981. (c) Miller, J. A.; Ullah, G. M.; Welsh, G. M.; Mallon, P. Tetrahedron Lett. 2001, 42, 2729-2731.