Oxidation of α-Alkoxy allenes into α′-alkoxy enones

Chemistry - A European Journal

Volumn 16, Issue 33, 2010, Pages 9973-9976

  Cordier, Pierre ^a   Aubert, Corinne ^a   Malacria, Max ^a   Gandon, Vincent ^a,b   Lacôte, Emmanuel ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

Allenes; Epoxidation; Ketones; Oxidation; Rearrangement

Indexed keywords

ALLENES; M-CHLOROPERBENZOIC ACID; OXYGEN ATOM; REARRANGEMENT; REGIO-SELECTIVE;

KETONES; OXIDATION; OXYGEN;

HYDROCARBONS;

EID: 77956125278     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000914     Document Type: Article

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57. This result is not consistent with a concerted migration as described in Scheme 2. It warrants further mechanistic determination. Nonetheless, we hypothesize that the opening of the allene oxide may require some activation (protonation or complexation of the oxygen atom), which would stabilize the enolate formed. The cation part of the zwitterion may thus have time to equilibrate to the most stable rotamer before collapsing to give the final product.
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