1,2-Halogen migration in haloallenyl ketones: Regiodivergent synthesis of halofurans

Journal of the American Chemical Society

Volumn 127, Issue 30, 2005, Pages 10500-10501

  Sromek, Anna W ^a   Rubina, Marina ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; FURAN DERIVATIVE; HALOGEN; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; ISOMERIZATION; MICHAEL ADDITION; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

ALKADIENES; CATALYSIS; CYCLIZATION; FURANS; HYDROCARBONS, HALOGENATED; KETONES;

EID: 23044485049     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053290y     Document Type: Article

References (41)

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20. See Supporting Information for details.
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38. This is in striking contrast to cycloisomerization of alkynyl imines, where significant loss of deuterium was observed. See: Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
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40. 3-catalyzed propargyl-allenyl isomerization (see ref 9) is responsible for partial incorporation of deuterium in position 3 of rf-2k (4 for rf-3k).
41. Much more sluggish reaction of 1j is in accordance with decreased ability of the Cl atom to form halirenium species b (Scheme 1).