1, 3-Dioxolan-2-ylium cations from acylfurans: Conversion of furyl ketones to esters under nonoxidative conditions
JA Bender, S Daves, FG West
Index: Bender, John A.; Daves, Samantha; West Tetrahedron Letters, 1998 , vol. 39, # 15 p. 2051 - 2054
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Citation Number: 4
Abstract
Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1, 2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1, 3-dioxolan-2-ylium cations 8. Subsequent ring-opening via SN2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1, 3-diol was employed, furan-containing ester 9 was formed instead of the standard product ...
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