Boron trichloride/tetra-n-butylammonium iodide: A mild, selective combination reagent for the cleavage of primary alkyl aryl ethers

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9719-9721

  Brooks, Paige R ^a   Wirtz, Michael C ^a   Vetelino, Michael G ^a   Rescek, Diane M ^a   Woodworth, Graeme F ^a   Morgan, Bradley P ^a   Coe, Jotham W ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL ARYL ETHER; AMMONIUM DERIVATIVE; BORON DERIVATIVE; IODINE DERIVATIVE; REAGENT;

ARTICLE; DEALKYLATION; DEGRADATION; REACTION ANALYSIS; REACTION TIME; STOICHIOMETRY;

EID: 0033601203     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9910740     Document Type: Article

References (49)

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36. 4NI from hot toluene to provide strictly anhydrous material. See: (a) Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Permagon Press Ltd.: Oxford, 1988; p 280, (b) Blau, R. J.; Espenson, J. H. J. Am. Chem. Soc. 1986, 108, 1962.
37. Unsatisfactory performance of this reagent combination is observed with 1-NH-indoles, nitro aromatics (partial nitro reduction), and some conjugated derivatives, such as 6-methoxytetralone (20, methyl stable to conditions, see text). Peculiar results have been observed with 2-bromo-1,3,5-trimethoxybenzene; debromination occurs, instead of ether cleavage and, after workup, provides the parent 1,3,5-trimethoxybenzene.
38. For cleavage of 6-methoxy-1-tetralone with 47% aq HBr, see: Bayer, H.; Batzl, C.; Hartmann, R. W.; Mannschreck, A. J. Med. Chem. 1991, 34, 2685.
39. 3 is observed at -12.6 ppm. These results suggest that direct boron-oxygen complex formation is a requirement for ether cleavage.
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46. 2.
47. Benzyl iodide and 3-methoxyphenol were isolated from the cleavage of 10. No benzyl chloride was detected (GC-MS).
48. 4NI with stoichiometric alkali metal halides have not met with success. Also see ref 11.
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