Intramolecular bromonium ion assisted epoxide ring-opening: Capture of the oxonium ion with an added external nucleophile

Journal of Organic Chemistry

Volumn 76, Issue 1, 2011, Pages 97-104

  Bonney, Karl J ^a   Braddock, D Christopher ^a   White, Andrew J P ^a   Yaqoob, Muhammad ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CBR; COMPETING PROCESS; DIASTEREOMERIC; N-BROMOSUCCINIMIDE; OXONIUM ION; RING OPENING; STEREOSPECIFIC; TETRAMETHYLGUANIDINE;

CARBOXYLIC ACIDS; ETHERS; NUCLEOPHILES; X RAY CRYSTALLOGRAPHY;

IONS;

ALCOHOL; BICYCLO COMPOUND; BROMINE; CARBOXYLIC ACID DERIVATIVE; EPOXIDE; GUANIDINE DERIVATIVE; HALIDE; HALOGEN; NUCLEOPHILE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIASTEREOISOMER; DILUTION; REACTION ANALYSIS; RING OPENING; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 78650891151     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101617h     Document Type: Article

References (34)

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24. 1H NMR monitoring of the reaction mixtures indicating that neither intermediate accumulates. The position of the expected rapid equilibrium between A and B is expected also to be concentration independent. One referee helpfully suggested that "If one makes the alternative assumption that bromonium ion A and oxonium ion B are not in rapid equilibrium, then the product distribution is the result of the relative rates of formation of B versus external nucleophilic attack on A. Higher dilution then favors the intramolecular attack to form B, which may then react with the added nucleophile at its leisure."
25. These alcohols have been reported previously as a 7:1 inseparable mixture, by bromination of an epoxydiol: Takahashi, A.; Aso, M.; Tanaka, M.; Suemune, H. Tetrahedron 2000, 56, 1999-2006
26. +.].
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31. 1H NMR and implies cocrystallisation.
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33. Ac2 ester hydrolysis.
34. Tetrafluorobenzoates 6c and 7c could be separated by HPLC and individually saponified to give pure samples of each of alcohols 6g and 7g (see Supporting Information).